dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c7fd9a87d9841b3ad10e4426fe85aca | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cccc(F)c1>>Cc1ccc2c(-c3cccc(F)c3)cnc(Nc3ccn(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.FC=1C=C(C=CC1)B(O)O.CN1N=C(C=C1)N>>FC=1C=C(C=CC1)C1=C2C=CC(=NC2=C(N=C1)NC1=NN(C=C1)C)C | Cl[c:16]1[n:15][cH:14][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:17][c:18]1[cH:19][cH:20][n:21]([CH3:22])[n:23]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]3)[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][cH:20][n... | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cccc(F)c1 | Cc1ccc2c(-c3cccc(F)c3)cnc(Nc3ccn(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 117bb42e263c78d4972cfd9400f5c94ee60c425fe51a73efd45cb9b04229693d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1ccc(-c2cnc(Nc3cc[nH]n3)c3ncccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[C;D1;H3:15]-[#7;a:16]1:[#7;a:17]:[c:18](-[NH2;D1;+0:19]):[c:20]:[c:21]:1>>[C;D1;H3:15]-[#7;a:16]1:[#7;a:17]:[c:18](-[NH;D2;+0:19]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[c;H0;D3;+0:4]... | null | [] | null | null | null | null | The title compound, MS: m/e=334.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-fluorophenylboronic acid and 1-methyl-1H-pyrazol-3-ylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccccc1 | c1ccccc1.c1cnc2cnccc2c1 | c1ccccc1.c1cnc2cnccc2c1.c1cc[nH]n1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cccc(F)c1>>Cc1ccc2c(-c3cccc(F)c3)cnc(Nc3ccn(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f64dd321d5b048fd88994162d80d2506 | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cncc(F)c1>>Cc1ccc2c(-c3cncc(F)c3)cnc(Nc3ccn(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.FC=1C=NC=C(C1)B(O)O.CN1N=C(C=C1)N>>FC=1C=C(C=NC1)C1=C2C=CC(=NC2=C(N=C1)NC1=NN(C=C1)C)C | Cl[c:16]1[n:15][cH:14][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:17][c:18]1[cH:19][cH:20][n:21]([CH3:22])[n:23]1.OB(O)[c:7]1[cH:8][n:9][cH:10][c:11]([F:12])[cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][c:11]([F:12])[cH:13]3)[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][cH:20][n:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cncc(F)c1 | Cc1ccc2c(-c3cncc(F)c3)cnc(Nc3ccn(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3cc[nH]n3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[C;D1;H3:16]-[#7;a:17]1:[#7;a:18]:[c:19](-[NH2;D1;+0:20]):[c:21]:[c:22]:1>>[C;D1;H3:16]-[#7;a:17]1:[#7;a:18]:[c:19](-[NH;D2;+0:20]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[c;... | null | [] | null | null | null | null | The title compound, MS: m/e=335.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-fluoropyridine-5-boronic acid and 1-methyl-1H-pyrazol-3-ylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1cc[nH]n1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cncc(F)c1>>Cc1ccc2c(-c3cncc(F)c3)cnc(Nc3ccn(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6e4eb561f22414780591d9a8d2fb7f3 | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1cccc(Br)n1.Cc1nc(N)cs1>>Cc1cccc(-c2cnc(Nc3csc(C)n3)c3nc(C)ccc23)n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC1=NC(=CC=C1)C.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C1=NC(=CC=C1)C)NC=1N=C(SC1)C | OB(O)[c:7]1[cH:8][n:9][c:10](Cl)[c:18]2[n:19][c:20]([CH3:21])[cH:22][cH:23][c:24]12.Br[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:25]1.[NH2:11][c:12]1[cH:13][s:14][c:15]([CH3:16])[n:17]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][s:14][c:15]([CH3:16])[n:17]3)[c:18]3[n:19][c:20]([C... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1cccc(Br)n1.Cc1nc(N)cs1 | Cc1cccc(-c2cnc(Nc3csc(C)n3)c3nc(C)ccc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1ccc(-c2cnc(Nc3cscn3)c3ncccc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c;H0;D3;+0:9](-B(-O)-O):[c:10](:[c:11]):[c:12]:1:[#7;a:13]:[c:14].[NH2;D1;+0:15]-[c:16]1:[#7;a:17]:[c:18]:[#16;a:19]:[c:20]:1>>[c:14]:[#7;a:13]:[c:12]1:[c:10](:[c:11]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:8]:[#7... | null | [] | null | null | null | null | The title compound, MS: m/e=348.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 2-bromo-6-methylpyridine and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cscn1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1cccc(Br)n1.Cc1nc(N)cs1>>Cc1cccc(-c2cnc(Nc3csc(C)n3)c3nc(C)ccc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eacdd362c3974108bf482f341dff78bb | Brc1nccs1.Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3nccs3)c3ccc(C)nc23)n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC=1SC=CN1.NC=1SC=C(N1)C>>CC=1N=C(SC1)NC=1N=CC(=C2C=CC(=NC12)C)C=1SC=CN1 | Br[c:11]1[n:12][cH:13][cH:14][s:15]1.OB(O)[c:10]1[cH:9][n:8][c:7](Cl)[c:22]2[c:16]1[cH:17][cH:18][c:19]([CH3:20])[n:21]2.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:23]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[n:12][cH:13][cH:14][s:15]3)[c:16]3[cH:17][cH:18][c:19]([CH3:20])[n:21][c:22]23)[n:2... | Brc1nccs1.Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1 | Cc1csc(Nc2ncc(-c3nccs3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5cb4a861ea2d212e4392edfdf4b57a104d5afdbc0e05dbab6b699923f1965746 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3nccs3)c2c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c;H0;D3;+0:9](-B(-O)-O):[c:10](:[c:11]):[c:12]:1:[#7;a:13]:[c:14].[NH2;D1;+0:15]-[c:16]1:[#16;a:17]:[c:18]:[c:19]:[#7;a:20]:1>>[c:11]:[c:10]1:[c:12](:[#7;a:13]:[c:14]):[c;H0;D3;+0:6](-[NH;D2;+0:15]-[c:16]2:[#16;a:17]:[c:18]:[c:19]:[#... | null | [] | null | null | null | null | The title compound, MS: m/e=340.0 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 2-bromothiazole and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cscn1.c1cnc2cnccc2c1 | c1cscn1.c1cnc2cnccc2c1 | c1cscn1.c1cscn1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Brc1nccs1.Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3nccs3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d95738aac534a398da04c342b73eacb | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.Cn1cncc1Br>>Cc1csc(Nc2ncc(-c3cncn3C)c3ccc(C)nc23)n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC1=CN=CN1C.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1N(C=NC1)C)NC=1SC=C(N1)C | OB(O)[c:10]1[cH:9][n:8][c:7](Cl)[c:23]2[c:17]1[cH:18][cH:19][c:20]([CH3:21])[n:22]2.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:24]1.Br[c:11]1[cH:12][n:13][cH:14][n:15]1[CH3:16]>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][n:15]3[CH3:16])[c:17]3[cH:18][cH:19][c:20]([CH3:21])[n:... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.Cn1cncc1Br | Cc1csc(Nc2ncc(-c3cncn3C)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | aac20b7f96f5cadf63ebeea826fc0423059e69b324c895ca661c417f6b136781 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3cnc[nH]3)c2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:1-[C;D1;H3:6].Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-B(-O)-O):[c:11](:[c:12]):[c:13]:1:[#7;a:14]:[c:15].[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[C;D1;H3:6]-[#7;a:5]1:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10]1:[c:9]:[#7;a:8]:[c... | null | [] | null | null | null | null | The title compound, MS: m/e=337.3 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 5-bromo-1-methyl-1H-imidazole and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1c[nH]cn1 | c1c[nH]cn1.c1cnc2cnccc2c1 | c1cscn1.c1c[nH]cn1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.Cn1cncc1Br>>Cc1csc(Nc2ncc(-c3cncn3C)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08d8e1df9a2744acbf8f93a4b6b0245f | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cn1cncc1Br>>Cc1ccc2c(-c3cncn3C)cnc(Nc3csc(C)n3)c2n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC1=CN=CN1C.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1N(C=NC1)C)NC=1N=C(SC1)C | OB(O)[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]2[c:15](Cl)[n:14][cH:13]1.[NH2:16][c:17]1[cH:18][s:19][c:20]([CH3:21])[n:22]1.Br[c:7]1[cH:8][n:9][cH:10][n:11]1[CH3:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][n:11]3[CH3:12])[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][s:19][c:20]([CH3:21])[n:... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cn1cncc1Br | Cc1ccc2c(-c3cncn3C)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | aac20b7f96f5cadf63ebeea826fc0423059e69b324c895ca661c417f6b136781 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cscn3)ncc(-c3cnc[nH]3)c2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:1-[C;D1;H3:6].Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-B(-O)-O):[c:11](:[c:12]):[c:13]:1:[#7;a:14]:[c:15].[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[C;D1;H3:6]-[#7;a:5]1:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10]1:[c:9]:[#7;a:8]:[c... | null | [] | null | null | null | null | The title compound, MS: m/e=337.3 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 5-bromo-1-methyl-1H-imidazole and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1c[nH]cn1 | c1c[nH]cn1.c1cnc2cnccc2c1 | c1c[nH]cn1.c1cnc2cnccc2c1.c1cscn1 | HCl.Br-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cn1cncc1Br>>Cc1ccc2c(-c3cncn3C)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f39228ea28d434db4d6faf5140b443b | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1nsc(Br)n1>>Cc1ccc2c(-c3nc(C)ns3)cnc(Nc3csc(C)n3)c2n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC1=NC(=NS1)C.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C1=NC(=NS1)C)NC=1N=C(SC1)C | OB(O)[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]2[c:15](Cl)[n:14][cH:13]1.[NH2:16][c:17]1[cH:18][s:19][c:20]([CH3:21])[n:22]1.Br[c:7]1[n:8][c:9]([CH3:10])[n:11][s:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[n:8][c:9]([CH3:10])[n:11][s:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][s:19][c:20]([CH3:21])[n:... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1nsc(Br)n1 | Cc1ccc2c(-c3nc(C)ns3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3de570e5b7d0abb90620506514f5f41b48de3846940cebf611082b00158554d2 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cscn3)ncc(-c3ncns3)c2c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[#7;a:3]:[c:4]:[#7;a:5]:1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c;H0;D3;+0:9](-B(-O)-O):[c:10](:[c:11]):[c:12]:1:[#7;a:13]:[c:14].[NH2;D1;+0:15]-[c:16]1:[#7;a:17]:[c:18]:[#16;a:19]:[c:20]:1>>[c:14]:[#7;a:13]:[c:12]1:[c:10](:[c:11]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]2:[#16;a:2]:[#7;a:3]:[c:4]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=355.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 5-bromo-3-methyl-[1,2,4]thiadiazole (Example M) and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ncsn1 | c1ncsn1.c1cnc2cnccc2c1 | c1ncsn1.c1cnc2cnccc2c1.c1cscn1 | HCl.Br-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1nsc(Br)n1>>Cc1ccc2c(-c3nc(C)ns3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93418a0b20b74152a9703a735a9b061b | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1ncc(Br)cn1>>Cc1ccc2c(-c3cnc(C)nc3)cnc(Nc3csc(C)n3)c2n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC=1C=NC(=NC1)C.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC(=NC1)C)NC=1N=C(SC1)C | OB(O)[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]2[c:16](Cl)[n:15][cH:14]1.[NH2:17][c:18]1[cH:19][s:20][c:21]([CH3:22])[n:23]1.Br[c:7]1[cH:8][n:9][c:10]([CH3:11])[n:12][cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][c:10]([CH3:11])[n:12][cH:13]3)[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][s:20][c:... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1ncc(Br)cn1 | Cc1ccc2c(-c3cnc(C)nc3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cscn3)ncc(-c3cncnc3)c2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-B(-O)-O):[c:11](:[c:12]):[c:13]:1:[#7;a:14]:[c:15].[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:15]:[#7;a:14]:[c:13]1:[c:11](:[c:12]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=349.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 5-bromo-2-methylpyrimidine and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1cscn1 | HCl.Br-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1ncc(Br)cn1>>Cc1ccc2c(-c3cnc(C)nc3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bed42bb7a9e14143a5b8bb7959385cd7 | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Ic1cnccn1>>Cc1ccc2c(-c3cnccn3)cnc(Nc3csc(C)n3)c2n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.IC1=NC=CN=C1.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C1=NC=CN=C1)NC=1N=C(SC1)C | OB(O)[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]2[c:15](Cl)[n:14][cH:13]1.[NH2:16][c:17]1[cH:18][s:19][c:20]([CH3:21])[n:22]1.I[c:7]1[cH:8][n:9][cH:10][cH:11][n:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][cH:11][n:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][s:19][c:20]([CH3:21])[n:22]... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Ic1cnccn1 | Cc1ccc2c(-c3cnccn3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5950257ab08e8d9b6c815d9a02e9fe074cc6e7ed65300a4d37c0cc4c184646bc | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cscn3)ncc(-c3cnccn3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-B(-O)-O):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].I-[c;H0;D3;+0:10]1:[#7;a:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[#7;a:11]:[c:12]:[c:13]:[#7;a:14... | null | [] | null | null | null | null | The title compound, MS: m/e=335.4 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 2-iodopyrazine and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cnccn1 | c1cnccn1.c1cnc2cnccc2c1 | c1cnccn1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Ic1cnccn1>>Cc1ccc2c(-c3cnccn3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66faef90f8194b22aa7973d76b8e5556 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cncc(F)c1>>Cc1ccc2c(-c3cncc(F)c3)cnc(Nc3csc(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.FC=1C=NC=C(C1)B(O)O.NC=1N=C(SC1)C>>FC=1C=C(C=NC1)C1=C2C=CC(=NC2=C(N=C1)NC=1N=C(SC1)C)C | Cl[c:16]1[n:15][cH:14][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:17][c:18]1[cH:19][s:20][c:21]([CH3:22])[n:23]1.OB(O)[c:7]1[cH:8][n:9][cH:10][c:11]([F:12])[cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][c:11]([F:12])[cH:13]3)[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][s:20][c:21]... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cncc(F)c1 | Cc1ccc2c(-c3cncc(F)c3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3cscn3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=352.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-fluoropyridine-5-boronic acid and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cncc(F)c1>>Cc1ccc2c(-c3cncc(F)c3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20ce52d0317e489b94bbf3070c4941a5 | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(C(F)(F)F)cs1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3nc(C(F)(F)F)cs3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CC(=CC=C1)B(O)O.NC=1SC=C(N1)C(F)(F)F>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC=CC1)NC=1SC=C(N1)C(F)(F)F | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:27][c:26]21.[NH2:16][c:17]1[n:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][s:25]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[n:18][c:19](... | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(C(F)(F)F)cs1.OB(O)c1cccnc1 | Cc1ccc2c(-c3cccnc3)cnc(Nc3nc(C(F)(F)F)cs3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=388.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-pyridineboronic acid and 2-amino-4-(trifluoromethyl)thiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(C(F)(F)F)cs1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3nc(C(F)(F)F)cs3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6cf3787ccdd846e7a4251d8aecc5c38f | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.FC(F)(F)c1cncc(Br)c1>>Cc1csc(Nc2ncc(-c3cncc(C(F)(F)F)c3)c3ccc(C)nc23)n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC=1C=NC=C(C1)C(F)(F)F.NC=1SC=C(N1)C>>CC=1N=C(SC1)NC=1N=CC(=C2C=CC(=NC12)C)C=1C=NC=C(C1)C(F)(F)F | OB(O)[c:10]1[cH:9][n:8][c:7](Cl)[c:27]2[c:21]1[cH:22][cH:23][c:24]([CH3:25])[n:26]2.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:28]1.Br[c:11]1[cH:12][n:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][c:15]([C:16]([F:17])([F:18... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.FC(F)(F)c1cncc(Br)c1 | Cc1csc(Nc2ncc(-c3cncc(C(F)(F)F)c3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-B(-O)-O):[c:11](:[c:12]):[c:13]:1:[#7;a:14]:[c:15].[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:12]:[c:11]1:[c:13](:[#7;a:14]:[c:15]):[c;H0;D3;+0:7](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]... | null | [] | null | null | null | null | The title compound, MS: m/e=402.3 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 3-bromo-5-(trifluoromethyl)pyridine and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.FC(F)(F)c1cncc(Br)c1>>Cc1csc(Nc2ncc(-c3cncc(C(F)(F)F)c3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bdcfb67bcbc4b75ae2faabb8da8f78a | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.FC(F)(F)c1cncc(I)n1>>Cc1csc(Nc2ncc(-c3cncc(C(F)(F)F)n3)c3ccc(C)nc23)n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.IC1=NC(=CN=C1)C(F)(F)F.NC=1SC=C(N1)C>>CC=1N=C(SC1)NC=1N=CC(=C2C=CC(=NC12)C)C1=NC(=CN=C1)C(F)(F)F | OB(O)[c:10]1[cH:9][n:8][c:7](Cl)[c:27]2[c:21]1[cH:22][cH:23][c:24]([CH3:25])[n:26]2.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:28]1.I[c:11]1[cH:12][n:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][c:15]([C:16]([F:17])([F:18])... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.FC(F)(F)c1cncc(I)n1 | Cc1csc(Nc2ncc(-c3cncc(C(F)(F)F)n3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5950257ab08e8d9b6c815d9a02e9fe074cc6e7ed65300a4d37c0cc4c184646bc | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3cnccn3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-B(-O)-O):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].I-[c;H0;D3;+0:10]1:[#7;a:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:6]:[c:5]1:[c:7](:[#7;a:8]:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#... | null | [] | null | null | null | null | The title compound, MS: m/e=403.3 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 2-iodo-6-trifluoromethyl-pyrazine (Example O) and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cnccn1 | c1cnccn1.c1cnc2cnccc2c1 | c1cscn1.c1cnccn1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1csc(N)n1.FC(F)(F)c1cncc(I)n1>>Cc1csc(Nc2ncc(-c3cncc(C(F)(F)F)n3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa36a447ff8b4421940d3e4f44879bc2 | Cc1ccc2cc[nH]c(=O)c2n1.O=P(Cl)(Cl)Cl>>Cc1ccc2ccnc(Cl)c2n1 | CC1=NC=2C(NC=CC2C=C1)=O.P(=O)(Cl)(Cl)Cl>>ClC=1N=CC=C2C=CC(=NC12)C | O=[c:9]1[nH:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:12][c:11]21.O=P(Cl)(Cl)[Cl:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[n:12]1 | Cc1ccc2cc[nH]c(=O)c2n1.O=P(Cl)(Cl)Cl | Cc1ccc2ccnc(Cl)c2n1 | null | null | null | Functional Group Interconversion | OtherReaction | 1533320419d12d201a2da7c530af5cdecf2d22c40d4aea3e0e5d401e4256abfc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2cnccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1:[#7;a:8]:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1:[#7;a:8]:[c:9] | 89 | [{"value": 89.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 4 | HOUR | A suspension of 2-Methyl-7H-[1,7]naphthyridin-8-one (820 mg, 5.12 mmol) and phosphorus oxychloride (7 ml, 76.8 mmol) was stirred at 90° C. for 4 hours. The reaction mixture was evaporated to dryness, poured on ice and set alkaline with aqueous ammonia. A red solution resulted. The aqueous layer was extracted with dichl... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ccncc2n1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | HCl | null | 90 | 4 | Cc1ccc2cc[nH]c(=O)c2n1.O=P(Cl)(Cl)Cl>>Cc1ccc2ccnc(Cl)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b8d0b48d52746f0ac11612a6701e8e3 | Cc1ccc2cc[nH]c(=O)c2n1.O=C1CCC(=O)N1I>>Cc1ccc2c(I)c[nH]c(=O)c2n1 | CC1=NC=2C(NC=CC2C=C1)=O.IN1C(CCC1=O)=O>>IC=1C=2C=CC(=NC2C(NC1)=O)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:8][nH:9][c:10](=[O:11])[c:12]2[n:13]1.O=C1CCC(=O)N1[I:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([I:7])[cH:8][nH:9][c:10](=[O:11])[c:12]2[n:13]1 | Cc1ccc2cc[nH]c(=O)c2n1.O=C1CCC(=O)N1I | Cc1ccc2c(I)c[nH]c(=O)c2n1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 6faf7c42d8db1d4ae0c42ba344dfd64924b8af11089303ab54e9eea41fd8f298 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1[nH]ccc2cccnc12 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[c:2]:[#7;a:3]:[c:4]1:[c:5]:[#7;a:6]:[c:7]:[cH;D2;+0:8]:[c:9]:1:[c:10]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5]:[c:4](:[#7;a:3]:[c:2]):[c:9]:1:[c:10] | 80.1 | [{"value": 80.0, "product": "IC=1C=2C=CC(=NC2C(NC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "IC=1C=2C=CC(=NC2C(NC1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2-Methyl-7H-[1,7]naphthyridin-8-one (10.0 g, 62.4 mmol) was suspended in 300 ml acetonitrile and N-iodosuccinimide (16.9 g, 74.9 mmol) was added. The suspension was stirred for 3 hours at reflux. The reaction mixture was cooled to room temperature and filtered. The solid was washed with acetonitrile and dried for 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2ccncc2n1.C1CCNC1 | c1ccc2ccncc2n1 | c1ccc2ccncc2n1 | HO- | C(C)#N | null | 3 | Cc1ccc2cc[nH]c(=O)c2n1.O=C1CCC(=O)N1I>C(C)#N>Cc1ccc2c(I)c[nH]c(=O)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2024d10d3364455091c7b11b5c6900c9 | Cc1ccc2c(I)c[nH]c(=O)c2n1.O=P(Cl)(Cl)Cl>>Cc1ccc2c(I)cnc(Cl)c2n1 | IC=1C=2C=CC(=NC2C(NC1)=O)C.P(=O)(Cl)(Cl)Cl>>ClC=1N=CC(=C2C=CC(=NC12)C)I | O=[c:10]1[nH:9][cH:8][c:6]([I:7])[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:13][c:12]21.O=P(Cl)(Cl)[Cl:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([I:7])[cH:8][n:9][c:10]([Cl:11])[c:12]2[n:13]1 | Cc1ccc2c(I)c[nH]c(=O)c2n1.O=P(Cl)(Cl)Cl | Cc1ccc2c(I)cnc(Cl)c2n1 | null | null | null | Functional Group Interconversion | OtherReaction | 1533320419d12d201a2da7c530af5cdecf2d22c40d4aea3e0e5d401e4256abfc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2cnccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1:[#7;a:8]:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1:[#7;a:8]:[c:9] | 32 | [{"value": 32.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 5 | HOUR | 5-Iodo-2-methyl-7H-[1,7]naphthyridin-8-one (14.2 g, 49.8 mmol) was suspended in phosphorus oxychloride (68 ml, 750 mmol) and stirred for 5 hours at 90° C. The reaction mixture was cooled to room temperature and evaporated to dryness. The residue was taken up in dichloromethane and extracted carefully with saturated NaH... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ccncc2n1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | HCl | null | 90 | 5 | Cc1ccc2c(I)c[nH]c(=O)c2n1.O=P(Cl)(Cl)Cl>>Cc1ccc2c(I)cnc(Cl)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15064e6f9a344bebb8a4e5e6287feab5 | CC(C)OB(OC(C)C)OC(C)C.Cc1ccc2c(I)cnc(Cl)c2n1>>Cc1ccc2c(B(O)O)cnc(Cl)c2n1 | Cl.ClC=1N=CC(=C2C=CC(=NC12)C)I.C(C)(C)OB(OC(C)C)OC(C)C.C(CCC)[Li]>>ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O | CC(C)O[B:7]([O:8]C(C)C)[O:9]C(C)C.I[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:15][c:14]2[c:12]([Cl:13])[n:11][cH:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([B:7]([OH:8])[OH:9])[cH:10][n:11][c:12]([Cl:13])[c:14]2[n:15]1 | CC(C)OB(OC(C)C)OC(C)C.Cc1ccc2c(I)cnc(Cl)c2n1 | Cc1ccc2c(B(O)O)cnc(Cl)c2n1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | b4534164a595ba03cada98d840ee2ea59801e889946d35f92d3fed21da1f4fc5 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1cnc2cnccc2c1 | C-C(-C)-O-[B;H0;D3;+0:1](-[O;H0;D2;+0:2]-C(-C)-C)-[O;H0;D2;+0:3]-C(-C)-C.I-[c;H0;D3;+0:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8](:[#7;a:9]:[c:10]):[c:11]:1:[c:12]>>[OH;D1;+0:2]-[B;H0;D3;+0:1](-[OH;D1;+0:3])-[c;H0;D3;+0:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8](:[#7;a:9]:[c:10]):[c:11]:1:[c:12] | 58 | [{"value": 58.0, "product": "ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -75 | CELSIUS | 1 | HOUR | 8-Chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I) (2.5 g, 8.2 mmol) and triisopropylborate (1.9 ml, 8.2 mmol) were dissolved in 80 ml THF and cooled to −75° C. n-Butyllithium (1.6M in hexane) (5.1 ml, 8.2 mmol) was added drop wise at −70° C. The reaction mixture was stirred for 1 hour at −75° C. and for 1 hour wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | HI | C1CCOC1 | -75 | 1 | CC(C)OB(OC(C)C)OC(C)C.Cc1ccc2c(I)cnc(Cl)c2n1>C1CCOC1>Cc1ccc2c(B(O)O)cnc(Cl)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-054c0bf3890b4d6aae392ca69d1292e4 | CC(C)(C)OC(=O)Nc1nc(CO)cs1>>CC(C)(C)OC(=O)Nc1nc(C=O)cs1 | C(C)(C)(C)OC(NC=1SC=C(N1)CO)=O>>C(C)(C)(C)OC(NC=1SC=C(N1)C=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]([CH2:12][OH:13])[cH:14][s:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]([CH:12]=[O:13])[cH:14][s:15]1 | CC(C)(C)OC(=O)Nc1nc(CO)cs1 | CC(C)(C)OC(=O)Nc1nc(C=O)cs1 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cscn1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1 | 78 | [{"value": 78.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (4-Hydroxymethyl-thiazol-2-yl)-carbamic acid tert-butyl ester (1.62 g, 6.95 mmol) was dissolved in 30 ml dichloromethane. Mangan(IV)oxid (3.65 g, 41.7 mmol) was added and the reaction mixture stirred at reflux for 2 hrs. The suspension was filtered through a dicalite speed plus pad and washed with dichloromethane. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cscn1 | null | ClCCl | null | null | CC(C)(C)OC(=O)Nc1nc(CO)cs1>ClCCl>CC(C)(C)OC(=O)Nc1nc(C=O)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57d9c9ef45a44c71ae2038d25d454b2c | CCOC=C(C(=O)OCC)C(=O)OCC.COc1ccc(N)cn1>>CCOC(=O)C(=CNc1ccc(OC)nc1)C(=O)OCC | NC=1C=CC(=NC1)OC.C(C)OC=C(C(=O)OCC)C(=O)OCC>>C(C)OC(C(C(=O)OCC)=CNC=1C=NC(=CC1)OC)=O | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:17](=[O:18])[O:19][CH2:20][CH3:21].[NH2:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[n:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][NH:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[n:15][cH:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21] | CCOC=C(C(=O)OCC)C(=O)OCC.COc1ccc(N)cn1 | CCOC(=O)C(=CNc1ccc(OC)nc1)C(=O)OCC | null | null | CCO | Protection | OtherReaction | a30e09b44595d9848d23bccfa80aef09bfec804d1c228009db3dc7ec0c35e4c2 | 247e2972c715851f1930f8effe0b723ab6b023606987ae3d24344cbb0208d390 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]:[#7;a:16]:[c:17]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C:3](=[CH;D2;+0:4]-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]:[#7;a:16]:[c:17])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[... | 100.3 | [{"value": 100.3, "product": "C(C)OC(C(C(=O)OCC)=CNC=1C=NC(=CC1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-amino-2-methoxypyridine (Aldrich, 100 g, 0.806 mole) and diethyl ethoxymethylenemalonate (Aldrich, 163 mL, 0.806 mole) in EtOH (1 L) was heated at reflux for 4 h, then was cooled to RT. Concentration to dryness gave the title compound (238 g, quantitative).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary amine | Enamine.Ester | null | null | c1ccncc1 | HO- | CCO | null | null | CCOC=C(C(=O)OCC)C(=O)OCC.COc1ccc(N)cn1>CCO>CCOC(=O)C(=CNc1ccc(OC)nc1)C(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf396f9ea4464d15b63e42279d599b4f | CCOC(=O)C(=CNc1ccc(OC)nc1)C(=O)OCC>>CCOC(=O)c1c[nH]c2ccc(OC)nc2c1=O | C(C)OC(C(C(=O)OCC)=CNC=1C=NC(=CC1)OC)=O>>C(C)OC(=O)C1=CNC2=CC=C(N=C2C1=O)OC | CCO[C:17]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][NH:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[n:15][cH:16]1)=[O:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[n:15][c:16]2[c:17]1=[O:18] | CCOC(=O)C(=CNc1ccc(OC)nc1)C(=O)OCC | CCOC(=O)c1c[nH]c2ccc(OC)nc2c1=O | null | null | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | Aromatic Heterocycle Formation | OtherReaction | 1893840d130702ee3f8535879c8e9d5f68683cac3dd9193f3d4d7e8a6d5776dd | 1e6c20da2513a958a8d4e8d5cc5b2d96f0a98f9170a0ea1256659b09d0ea8cf1 | O=c1cc[nH]c2cccnc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[NH;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[#7;a:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[nH;D2;+0:5]:[c:6](:[c:7]):[c;H0;D3;+0:8](:[#7;a:9]:[c:10]):[c;H0;D3;+0:1]:1=[O;D1;H0:2] | 73.1 | [{"value": 73.0, "product": "C(C)OC(=O)C1=CNC2=CC=C(N=C2C1=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "C(C)OC(=O)C1=CNC2=CC=C(N=C2C1=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dowtherm A (Fluka, 500 mL) was brought to boiling (250° C.) in a 2 L 3-neck flask fitted with a still-head and a reflux condenser. 2-[(6-Methoxypyridin-3-ylamino)methylene]malonic acid diethyl ester (100 g, 0.34 mole) was added portion-wise over 5 min. The solution was heated at reflux for an additional 15 min, allowin... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Ester | c1ccncc1 | c1cc2ncccc2nc1 | c1cc2ncccc2nc1 | HO- | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | null | null | CCOC(=O)C(=CNc1ccc(OC)nc1)C(=O)OCC>C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2>CCOC(=O)c1c[nH]c2ccc(OC)nc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b92e284ffb8418a9f8c76a9774af3b0 | BrP(Br)Br.CCOC(=O)c1c[nH]c2ccc(OC)nc2c1=O>>CCOC(=O)c1cnc2ccc(OC)nc2c1Br | C([O-])([O-])=O.[Na+].[Na+].P(Br)(Br)Br.C(C)OC(=O)C1=CNC2=CC=C(N=C2C1=O)OC.O>>C(C)OC(=O)C=1C=NC2=CC=C(N=C2C1Br)OC | BrP(Br)[Br:18].O=[c:17]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[n:15][c:16]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[n:15][c:16]2[c:17]1[Br:18] | BrP(Br)Br.CCOC(=O)c1c[nH]c2ccc(OC)nc2c1=O | CCOC(=O)c1cnc2ccc(OC)nc2c1Br | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 2beba888e0a16c73c644bbcb698f0ead29c4f4e028773e48e32ce1712c71899e | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2cccnc2c1 | Br-P(-Br)-[Br;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3](:[#7;a:4]:[c:5]):[c:6](:[c:7]):[nH;D2;+0:8]:[c:9]:[c:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3](:[#7;a:4]:[c:5]):[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | 90 | [{"value": 90.0, "product": "C(C)OC(=O)C=1C=NC2=CC=C(N=C2C1Br)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "C(C)OC(=O)C=1C=NC2=CC=C(N=C2C1Br)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A suspension of 6-methoxy-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmol) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately room temperature—may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmol) w... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc2ncccc2nc1 | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | HBr | CN(C)C=O | null | 0.5 | BrP(Br)Br.CCOC(=O)c1c[nH]c2ccc(OC)nc2c1=O>CN(C)C=O>CCOC(=O)c1cnc2ccc(OC)nc2c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-663dd6439ed14536af60690a5c94cea0 | CCOC(=O)c1cnc2ccc(OC)nc2c1Br>>COc1ccc2ncc(C(=O)O)c(Br)c2n1 | [OH-].[Na+].C(C)OC(=O)C=1C=NC2=CC=C(N=C2C1Br)OC.Cl>>BrC1=C(C=NC2=CC=C(N=C12)OC)C(=O)O | CC[O:12][C:10]([c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:16][c:15]2[c:13]1[Br:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13]([Br:14])[c:15]2[n:16]1 | CCOC(=O)c1cnc2ccc(OC)nc2c1Br | COc1ccc2ncc(C(=O)O)c(Br)c2n1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cnc2cccnc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | 2 N NaOH (300 mL, 600 mmol) was added dropwise over 30 min to a stirred solution of 4-bromo-6-methoxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (83.56 g, 268 mmol) in THF (835 mL). Stirring was continued overnight, at which time LC/MS showed that the saponification was complete. 2 N HCl was added to pH 6 and the... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2cccnc2c1 | Other | C1CCOC1 | null | 8 | CCOC(=O)c1cnc2ccc(OC)nc2c1Br>C1CCOC1>COc1ccc2ncc(C(=O)O)c(Br)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67ae07d991f2408792fe0f7e73cc3065 | COc1ccc2ncc(N)c(Br)c2n1>>COc1ccc2ncc([N+]#N)c(Br)c2n1 | BrC1=C(C=NC2=CC=C(N=C12)OC)N.F[B-](F)(F)F.N#[O+]>>F[B-](F)(F)F.BrC1=C(C=NC2=CC=C(N=C12)OC)[N+]#N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([NH2:10])[c:12]([Br:13])[c:14]2[n:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([N+:10]#[N:11])[c:12]([Br:13])[c:14]2[n:15]1 | COc1ccc2ncc(N)c(Br)c2n1 | COc1ccc2ncc([N+]#N)c(Br)c2n1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 4b9613e8eb03ba0ca635945a60e7b18985445e9967460b2f7cd3bfa7398bb2a3 | ca5105ff0b33557e585dc54e7cfdd7fa7df4e7f9c3edc13b706f4674b75a100e | c1cnc2cccnc2c1 | [#7;a:1]:[c:2]1:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6]:[#7;a:7]:[c:8]:1>>[#7;a:1]:[c:2]1:[c:3]:[c:4](-[N+;H0;D2:5]#[N;D1;H0:9]):[c:6]:[#7;a:7]:[c:8]:1 | 90 | [{"value": 90.0, "product": "F[B-](F)(F)F.BrC1=C(C=NC2=CC=C(N=C12)OC)[N+]#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "F[B-](F)(F)F.BrC1=C(C=NC2=CC=C(N=C12)OC)[N+]#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-bromo-6-methoxy-[1,5]naphthyridin-3-ylamine (25.2 g, 99.2 mmol) in dry THF (400 mL) was maintained at −5° C. while nitrosonium tetrafluoroborate (12.9 g, 110 mmol) was added portion-wise over 30 min (approximately 2 g portions). The reaction was continued for an additional 1 h at −5° C., at which time T... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | null | null | c1cnc2cccnc2c1 | null | C1CCOC1 | null | 1 | COc1ccc2ncc(N)c(Br)c2n1>C1CCOC1>COc1ccc2ncc([N+]#N)c(Br)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88ecf83980764c31929236f79b1c078a | COc1ccc2ncc([N+]#N)c(Br)c2n1>>COc1ccc2ncc(F)c(Br)c2n1 | F[B-](F)(F)F.BrC1=C(C=NC2=CC=C(N=C12)OC)[N+]#N>>BrC1=C(C=NC2=CC=C(N=C12)OC)F | N#[N+][c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:14][c:13]2[c:11]1[Br:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([Br:12])[c:13]2[n:14]1 | COc1ccc2ncc([N+]#N)c(Br)c2n1 | COc1ccc2ncc(F)c(Br)c2n1 | null | null | C1CCCC2CCCCC12.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | c161fe806ec0c1657c121e971047393b32c73d5c613d43b95ffeb21ac3008186 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2cccnc2c1 | N#[N+]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[c:8]:1-[Br;D1;H0:9]>>[Br;D1;H0:9]-[c:8]1:[c:5](:[#7;a:6]:[c:7]):[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[F;D1;H0:10] | 40 | [{"value": 40.0, "product": "BrC1=C(C=NC2=CC=C(N=C12)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "BrC1=C(C=NC2=CC=C(N=C12)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 5 | MINUTE | A suspension of 4-bromo-6-methoxy-[1,5]naphthyridine-3-diazonium tetrafluoroborate (31.42 g, 89.0 mmol) in decalin (mixed isomers, 500 mL) in a 2 L flask* was heated to 180° C. and held at this temperature for 5 min. The mixture was cooled and diluted with CHCl3 (500 mL, to keep the product in solution), and the result... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | Other | C1CCCC2CCCCC12.C(Cl)(Cl)Cl | 180 | 0.083333 | COc1ccc2ncc([N+]#N)c(Br)c2n1>C1CCCC2CCCCC12.C(Cl)(Cl)Cl>COc1ccc2ncc(F)c(Br)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b0711cdd8aa468687b4baaf6c8ff36f | COCCOC.COc1ccc2ncc(F)c(Br)c2n1>>C=Cc1c(F)cnc2ccc(OC)nc12 | BrC=1C(=CN=C2C=CC(=NC12)OC)F.C([O-])([O-])=O.[K+].[K+].COCCOC>>C(=C)C=1C(=CN=C2C=CC(=NC12)OC)F | COCCO[CH3:1].Br[c:3]1[c:4]([F:5])[cH:6][n:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[n:14][c:15]12>>[CH2:1]=[CH:2][c:3]1[c:4]([F:5])[cH:6][n:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[n:14][c:15]12 | COCCOC.COc1ccc2ncc(F)c(Br)c2n1 | C=Cc1c(F)cnc2ccc(OC)nc12 | null | null | O | C-C Coupling | OtherReaction | 259dac5d2ba0859c4705c9e771eb45b85b495920bfc1b793b5f2fa18dea8f344 | 23c65ae2aa282ff569a38af7d0cad288cbe289bcf57e497c7f4b894b7dbcb571 | c1cnc2cccnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3]:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]:[c:9]:1-[F;D1;H0:10].C-O-C-C-O-[CH3;D1;+0:11]>>[CH2;D1;+0:11]=[C:12]-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3]:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]:[c:9]:1-[F;D1;H0:10] | 90 | [{"value": 90.0, "product": "C(=C)C=1C(=CN=C2C=CC(=NC12)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 10 | HOUR | To a solution of 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine (2.0 g, 7.81 mmol), potassium carbonate (1.08 g, 7.81 mmol), tetrakis-triphenylphosphine (90 mg, 0.08 mmol) in DME (60 mL) and H2O (20 mL) was added 2,4,6-trivinylcycloborane-pyridine complex (0.94 g, 3.91 mmol). After stirring for 10 h at 85° C. the rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Vinyl | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | HBr | O | 85 | 10 | COCCOC.COc1ccc2ncc(F)c(Br)c2n1>O>C=Cc1c(F)cnc2ccc(OC)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c531e295cec45a6bf35d682e7d2d03e | COCCOC.COc1ccc2nccc(OS(=O)(=O)C(F)(F)F)c2n1>>C=Cc1ccnc2ccc(OC)nc12 | FC(S(=O)(=O)OC1=CC=NC2=CC=C(N=C12)OC)(F)F.C(=O)([O-])[O-].[K+].[K+].COCCOC>>C(=C)C=1C=CN=C2C=CC(=NC12)OC | COCCO[CH3:1].O=S(=O)(O[c:3]1[cH:4][cH:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[n:13][c:14]12)C(F)(F)F>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[n:13][c:14]12 | COCCOC.COc1ccc2nccc(OS(=O)(=O)C(F)(F)F)c2n1 | C=Cc1ccnc2ccc(OC)nc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | OtherReaction | a076454a03e006bafb9ea53bd98499d0d417e297c51e84c7797583a4064b8a9f | 7712a2024fe04bf99cd62192c71686447a6b12d3c5c8ec1e1eee09f27863175f | c1cnc2cccnc2c1 | C-O-C-C-O-[CH3;D1;+0:1].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10]>>[CH2;D1;+0:1]=[C:11]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10] | 81 | [{"value": 81.0, "product": "C(=C)C=1C=CN=C2C=CC(=NC12)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (from Prep. 2b) (5.0 g, 16.23 mmol) in DME (80 mL) and H2O (40 mL) was added trivinyl boronate (1.96 g, 8.1 mmol), K2CO3 (2.23 g, 16.23 mmol) and Pd(PPh3)4 (0.19 g, 0.16 mmol). After 3 h at 90° C. under N2, the reaction solution was concentr... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Ether.Ether | Vinyl | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | TfOH.HO- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | null | 3 | COCCOC.COc1ccc2nccc(OS(=O)(=O)C(F)(F)F)c2n1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>C=Cc1ccnc2ccc(OC)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ab07b7805064b1aad32e7610fd0d968 | CCOC(=O)CS.COC(=O)c1ccc(Br)c(N)n1>>COC(=O)c1ccc2c(n1)NC(=O)CS2 | SCC(=O)OCC.[H-].[Na+].NC1=C(C=CC(=N1)C(=O)OC)Br>>O=C1NC2=C(SC1)C=CC(=N2)C(=O)OC | CCO[C:12](=[O:13])[CH2:14][SH:15].Br[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:10][c:9]1[NH2:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[NH:11][C:12](=[O:13])[CH2:14][S:15]2 | CCOC(=O)CS.COC(=O)c1ccc(Br)c(N)n1 | COC(=O)c1ccc2c(n1)NC(=O)CS2 | null | null | CN(C)C=O.CCOC(=O)C | Acylation | OtherReaction | fd7342aebd388ea0258590b8154abb6692348e465fe66bbcd1afc68573c01546 | 998b836dac7df9ef4e0c29fab0a2e58509223c9eecb587a6e49e6cb1927e3269 | O=C1CSc2cccnc2N1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#7;a:8]:[c:9]:1-[NH2;D1;+0:10].C-C-O-[C;H0;D3;+0:11](=[O;D1;H0:12])-[C:13]-[SH;D1;+0:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#7;a:8]:[c:9]2:[c;H0;D3;+0:1](:[c:2]:[c:3]:1)-[S;H0;D2;+0:14]-[C:13]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[NH;D2;+0:10]-2 | null | [] | null | null | 16 | HOUR | A solution of ethyl 2-mercaptoacetate (1.473 mL) in DMF (48 mL) was ice-cooled and treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 h methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T. R. Kelly and F. Lang, J. Org. Chem. 61, 1996, 4623-4633) was added and the mixture stirred for 16 h at room... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine.Aliphatic thiol | Secondary amide.Monosulfide | c1ccncc1 | c1cnc2c(c1)SCCN2 | c1cnc2c(c1)SCCN2 | HBr | CN(C)C=O.CCOC(=O)C | null | 16 | CCOC(=O)CS.COC(=O)c1ccc(Br)c(N)n1>CN(C)C=O.CCOC(=O)C>COC(=O)c1ccc2c(n1)NC(=O)CS2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7407fa980584470c98f8f90dd9061d57 | COC(=O)c1ccc2c(n1)NC(=O)CS2>>O=C1CSc2ccc(C(=O)O)nc2N1 | O=C1NC2=C(SC1)C=CC(=N2)C(=O)OC.O.[OH-].[Na+]>>O=C1NC2=C(SC1)C=CC(=N2)C(=O)O | C[O:11][C:9]([c:8]1[cH:7][cH:6][c:5]2[c:13]([n:12]1)[NH:14][C:2](=[O:1])[CH2:3][S:4]2)=[O:10]>>[O:1]=[C:2]1[CH2:3][S:4][c:5]2[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[n:12][c:13]2[NH:14]1 | COC(=O)c1ccc2c(n1)NC(=O)CS2 | O=C1CSc2ccc(C(=O)O)nc2N1 | null | null | O1CCOCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CSc2cccnc2N1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 86.1 | [{"value": 86.1, "product": "O=C1NC2=C(SC1)C=CC(=N2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (788 mg) in dioxan (120 ml)/water (30 mL) was treated dropwise over 2 h with 0.5M NaOH solution (8 mL) and stirred overnight. After evaporation to approx. 3 ml, water (5 mL) was added and 2M HCl to pH4. The precipitated solid was filtere... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2c(c1)SCCN2 | Other | O1CCOCC1 | null | 8 | COC(=O)c1ccc2c(n1)NC(=O)CS2>O1CCOCC1>O=C1CSc2ccc(C(=O)O)nc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1aed1d4e88604e91a6d221064a8618b0 | O=C1CSc2ccc(C(=O)O)nc2N1>>O=C1CSc2ccc(CO)nc2N1 | ClC(=O)OCC(C)C.O=C1NC2=C(SC1)C=CC(=N2)C(=O)O.C(C)N(CC)CC>>OCC=1C=CC=2SCC(NC2N1)=O | O=[C:9]([c:8]1[cH:7][cH:6][c:5]2[c:12]([n:11]1)[NH:13][C:2](=[O:1])[CH2:3][S:4]2)[OH:10]>>[O:1]=[C:2]1[CH2:3][S:4][c:5]2[cH:6][cH:7][c:8]([CH2:9][OH:10])[n:11][c:12]2[NH:13]1 | O=C1CSc2ccc(C(=O)O)nc2N1 | O=C1CSc2ccc(CO)nc2N1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C1CSc2cccnc2N1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]-[#7:7]>>[#7:7]-[c:6]:[#7;a:5]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:4] | 74.1 | [{"value": 74.1, "product": "OCC=1C=CC=2SCC(NC2N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (500 mg) in THF (24 mL) with triethylamine (0.396 mL) was cooled to −10° C. and isobutyl chloroformate (0.339 ml) was added. After 20 minutes the suspension was filtered through kieselguhr into an ice-cooled solution of sodium borohydride (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1cnc2c(c1)SCCN2 | Other | C1CCOC1 | null | 0.5 | O=C1CSc2ccc(C(=O)O)nc2N1>C1CCOC1>O=C1CSc2ccc(CO)nc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92b756c8dc184bee8a41fb43180dac2f | O=C1CSc2ccc(CO)nc2N1>>O=Cc1ccc2c(n1)NC(=O)CS2 | OCC=1C=CC=2SCC(NC2N1)=O.C1CCOC1>>O=C1NC2=C(SC1)C=CC(=N2)C=O | [OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([n:8]1)[NH:9][C:10](=[O:11])[CH2:12][S:13]2>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([n:8]1)[NH:9][C:10](=[O:11])[CH2:12][S:13]2 | O=C1CSc2ccc(CO)nc2N1 | O=Cc1ccc2c(n1)NC(=O)CS2 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C1CSc2cccnc2N1 | [#7:1]-[c:2]:[#7;a:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[c:7]>>[#7:1]-[c:2]:[#7;a:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7] | 55.1 | [{"value": 55.1, "product": "O=C1NC2=C(SC1)C=CC(=N2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-hydroxymethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine (330 mg) in dichloromethane (30 mL)/THF (30 mL) was treated with manganese dioxide (730 mg) and stirred at room temperature. Further manganese dioxide was added after 1 h (730 mg) and 16 h (300 mg). After a total of 20 h the mixture was filte... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cnc2c(c1)SCCN2 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].ClCCl | null | null | O=C1CSc2ccc(CO)nc2N1>[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].ClCCl>O=Cc1ccc2c(n1)NC(=O)CS2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d28d319d39441ada334f0a675ea1006 | CCOC=C(C(=O)OCC)C(=O)OCC.COc1ccc(N)cc1>>CCOC(=O)c1cnc2ccc(OC)cc2c1O | COC1=CC=C(N)C=C1.C(C)OC=C(C(=O)OCC)C(=O)OCC.C(C)O>>C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1O)OC | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:17](OCC)=[O:18].[NH2:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c:16]2[c:17]1[OH:18] | CCOC=C(C(=O)OCC)C(=O)OCC.COc1ccc(N)cc1 | CCOC(=O)c1cnc2ccc(OC)cc2c1O | null | null | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | Aromatic Heterocycle Formation | OtherReaction | e04d5084bd6bde4efb79456fdff70fdac6e2cf2829400707e635c879cfe5d271 | 4a985e8b872e7ba2e4af89799e804f05fef7f2382ed6af4bf801b35cf0e038a9 | c1ccc2ncccc2c1 | C-C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C-C.[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D2;+0:9]:[c:10](:[c:11]):[c;H0;D3;+0:12](:[c:13]:[c:14]):[c;H0;D3;+0:7]:1-[OH;D1;+0:8] | 78.9 | [{"value": 78.0, "product": "C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 4-methoxyaniline (40 g, 0.32 mole) and diethyl ethoxymethylenemalonate (65 mL, 0.32 mole) in Dowtherm A (500 mL) was heated at reflux in a flask fitted with side-arm and condenser, and heating was continued until all the ethanol had distilled off (ca. 0.5 hr). The solution was cooled and pentane was added... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary amine | Ester.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | null | 8 | CCOC=C(C(=O)OCC)C(=O)OCC.COc1ccc(N)cc1>C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2>CCOC(=O)c1cnc2ccc(OC)cc2c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c875076c222b479b98e5c168d008218c | BrP(Br)Br.CCOC(=O)c1cnc2ccc(OC)cc2c1O>>CCOC(=O)c1cnc2ccc(OC)cc2c1Br | P(Br)(Br)Br.C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1O)OC>>C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1Br)OC | BrP(Br)[Br:18].O[c:17]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c:16]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c:16]2[c:17]1[Br:18] | BrP(Br)Br.CCOC(=O)c1cnc2ccc(OC)cc2c1O | CCOC(=O)c1cnc2ccc(OC)cc2c1Br | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2ncccc2c1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]:[c:9]:1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]:[c:9]:1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13] | 78 | [{"value": 78.0, "product": "C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1Br)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.3, "product": "C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1Br)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | PBr3 (64.5 g, 22.5 mL, 0.239 mole) was added dropwise to a stirred, ice cold suspension of 4-hydroxy-6-methoxy-quinoline-3-carboxylic acid ethyl ester (59 g, 0.239 mole) in DMF (750 mL); the temperature rose to 15-20° C. for 30 min and then dropped to ca. 5° C. (the starting material dissolved fairly quickly and a new ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | CN(C)C=O | null | 0.5 | BrP(Br)Br.CCOC(=O)c1cnc2ccc(OC)cc2c1O>CN(C)C=O>CCOC(=O)c1cnc2ccc(OC)cc2c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4371dca6a9cd48b5826870e1ea301247 | CCOC(=O)c1cnc2ccc(OC)cc2c1Br>>COc1ccc2ncc(C(=O)O)c(Br)c2c1 | Cl.[OH-].[Na+].C(C)OC(=O)C=1C=NC2=CC=C(C=C2C1Br)OC.CO.C(Cl)Cl>>BrC1=C(C=NC2=CC=C(C=C12)OC)C(=O)O | CC[O:12][C:10]([c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][c:15]2[c:13]1[Br:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13]([Br:14])[c:15]2[cH:16]1 | CCOC(=O)c1cnc2ccc(OC)cc2c1Br | COc1ccc2ncc(C(=O)O)c(Br)c2c1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2ncccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 91.3 | [{"value": 91.0, "product": "BrC1=C(C=NC2=CC=C(C=C12)OC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "BrC1=C(C=NC2=CC=C(C=C12)OC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 4-Bromo-6-methoxy-quinoline-3-carboxylic acid ethyl ester (41 g, 0.132 mole), partially dissolved in THF (600 mL), was treated dropwise with aqueous 2 M sodium hydroxide (198.4 mL, 0.396 mole). After 24 hr, the reaction was complete by TLC (2% MeOH/CH2Cl2). The mixture was neutralized with 5 M HCl then the THF was remo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1 | Other | C1CCOC1 | null | 24 | CCOC(=O)c1cnc2ccc(OC)cc2c1Br>C1CCOC1>COc1ccc2ncc(C(=O)O)c(Br)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba57edd1b47e4d0899628028abc86b3d | CC(C)(C)O.COc1ccc2ncc(C(=O)O)c(Br)c2c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>COc1ccc2ncc(NC(=O)OC(C)(C)C)c(Br)c2c1 | BrC1=C(C=NC2=CC=C(C=C12)OC)C(=O)O.C(C)N(CC)CC.C(C)(C)(C)O.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>C(C)(C)(C)OC(NC=1C=NC2=CC=C(C=C2C1Br)OC)=O | [OH:13][C:14]([CH3:15])([CH3:16])[CH3:17].O[C:11]([c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]2[c:18]1[Br:19])=[O:12].[N-]=[N+]=[N:10]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([Br:19])[c:20]2... | CC(C)(C)O.COc1ccc2ncc(C(=O)O)c(Br)c2c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | COc1ccc2ncc(NC(=O)OC(C)(C)C)c(Br)c2c1 | null | null | CN(C)C=O | Protection | OtherReaction | b425438537ae8dc625817066544a88605008859add1968d4c333819464ddb7ec | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | c1ccc2ncccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[Br;D1;H0:9].O=P(-[N;H0;D2;+0:10]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[OH;D1;+0:15]>>[Br;D1;H0:9]-[c:8]1:[c:7]:[c:6]:[#7;a:5]:[c:4]:[c;H0;D3;+0:3]:1-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O... | 53 | [{"value": 53.0, "product": "C(C)(C)(C)OC(NC=1C=NC2=CC=C(C=C2C1Br)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 4-Bromo-6-methoxyquinoline-3-carboxylic acid (34 g, 0.121 mole), triethylamine (141 mL) and tert-butanol (181 mL) in dry DMF (400 mL) was added diphenylphosphoryl azide (36.6 g, 28.6 mL, 0.133 mole). The mixture was heated at 100° C. for 1 h (see Note), then cooled and concentrated. The residue was dis... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CN(C)C=O | 100 | null | CC(C)(C)O.COc1ccc2ncc(C(=O)O)c(Br)c2c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>CN(C)C=O>COc1ccc2ncc(NC(=O)OC(C)(C)C)c(Br)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdf39d02b5a74856ba86c03a72223844 | COc1ccc2ncc(NC(=O)OC(C)(C)C)c(Br)c2c1>>COc1ccc2ncc(N)c(Br)c2c1 | C(C)(C)(C)OC(NC=1C=NC2=CC=C(C=C2C1Br)OC)=O.FC(C(=O)O)(F)F>>NC=1C=NC2=CC=C(C=C2C1Br)OC | CC(C)(C)OC(=O)[NH:10][c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][c:13]2[c:11]1[Br:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([NH2:10])[c:11]([Br:12])[c:13]2[cH:14]1 | COc1ccc2ncc(NC(=O)OC(C)(C)C)c(Br)c2c1 | COc1ccc2ncc(N)c(Br)c2c1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2ncccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 101.1 | [{"value": 101.0, "product": "NC=1C=NC2=CC=C(C=C2C1Br)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.1, "product": "NC=1C=NC2=CC=C(C=C2C1Br)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | (4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl ester (22.7 g, 0.0643 mole) was dissolved in CH2Cl2 (200 mL) and treated with trifluoroacetic acid (100 mL). After 3.5 hr at RT, the mixture was concentrated and the residue was dissolved in water. The solution was made basic with aqueous sodium carbonate. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2ncccc2c1 | HO- | C(Cl)Cl | null | 3.5 | COc1ccc2ncc(NC(=O)OC(C)(C)C)c(Br)c2c1>C(Cl)Cl>COc1ccc2ncc(N)c(Br)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30bce440e33f465fba6e680951650d33 | COc1ccc2ncc(N)c(Br)c2c1>>COC1([N+]#N)CN=c2ccccc2=C1Br | NC=1C=NC2=CC=C(C=C2C1Br)OC.C1CCOC1.F[B-](F)(F)F.N#[O+]>>F[B-](F)(F)F.BrC=1C(CN=C2C=CC=CC12)(OC)[N+]#N | [CH3:1][O:2][c:11]1[cH:10][cH:9][c:8]2[n:7][cH:6][c:3]([NH2:4])[c:14]([Br:15])[c:13]2[cH:12]1>>[CH3:1][O:2][C:3]1([N+:4]#[N:5])[CH2:6][N:7]=[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2=[C:14]1[Br:15] | COc1ccc2ncc(N)c(Br)c2c1 | COC1([N+]#N)CN=c2ccccc2=C1Br | null | null | null | Reduction | OtherReaction | 7a81b28c0799eae8e6cc0339ec3ae224c333d9e303d3e8b4a87eea3157f0d76a | 333fc58cf70fc593825de0bc67f6f2934273458cd2a9695028f67d2225d9e489 | C1=c2ccccc2=NCC1 | [Br;D1;H0:1]-[c;H0;D3;+0:2]1:[c;H0;D3;+0:3]2:[c:4]:[c;H0;D3;+0:5](-[O;H0;D2;+0:6]-[C;D1;H3:7]):[c:8]:[c:9]:[c;H0;D3;+0:10]:2:[n;H0;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[NH2;D1;+0:14]>>[Br;D1;H0:1]-[C;H0;D3;+0:2]1=[c;H0;D3;+0:3]2:[c:4]:[cH;D2;+0:5]:[c:8]:[c:9]:[c;H0;D3;+0:10]:2=[N;H0;D2;+0:11]-[CH2;D2;+0:12]-[C;H0;... | 76 | [{"value": 76.0, "product": "F[B-](F)(F)F.BrC=1C(CN=C2C=CC=CC12)(OC)[N+]#N", "details": "PERCENTYIELD", "is_desired": false}] | -2.5 | CELSIUS | 30 | MINUTE | 3-Amino-4-bromo-6-methoxyquinoline (18.4 g, 0.0727 mole) was dissolved in dry THF (250 mL) and the solution was cooled to −8° C. (EtOH-ice bath). Nitrosonium tetrafluoroborate (9.34 g, 0.08 mole) was added in portions over 10 min, keeping the temperature less than −2° C. The mixture was stirred at −5 to 0° C. for 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary amine | Alkenyl halide.Ether | c1ccc2ncccc2c1 | C1=c2ccccc2=NCC1 | C1=c2ccccc2=NCC1 | null | null | -2.5 | 0.5 | COc1ccc2ncc(N)c(Br)c2c1>>COC1([N+]#N)CN=c2ccccc2=C1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-071f5f659bd1470ca1b928650f978793 | BrBr.O=[N+]([O-])c1ncccc1O>>O=[N+]([O-])c1nc(Br)ccc1O | OC=1C(=NC=CC1)[N+](=O)[O-].C[O-].[Na+].BrBr>>BrC1=NC(=C(C=C1)O)[N+](=O)[O-] | Br[Br:7].[O:1]=[N+:2]([O-:3])[c:4]1[n:5][cH:6][cH:8][cH:9][c:10]1[OH:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[n:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[OH:11] | BrBr.O=[N+]([O-])c1ncccc1O | O=[N+]([O-])c1nc(Br)ccc1O | null | null | CO | Functional Group Interconversion | Bromination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | Br-[Br;H0;D1;+0:1].[c:2]:[#7;a:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[#7;a:3]:[c:2]):[c:5]:[c:6] | 97.9 | [{"value": 96.0, "product": "BrC1=NC(=C(C=C1)O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "BrC1=NC(=C(C=C1)O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 3-Hydroxy-2-nitropyridine (20 g, 0.143 mole) was dissolved in methanol (400 mL) and a solution of 25% sodium methoxide in methanol (33 mL, 0.13 mole) was added at room temperature. The mixture was stirred for 30 min, then was cooled to 0° C., and bromine (7.2 mL, 0.14 mole) was added slowly. The reaction was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | CO | 0 | 0.5 | BrBr.O=[N+]([O-])c1ncccc1O>CO>O=[N+]([O-])c1nc(Br)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-657ae7c1e91d442685440e846627d57c | CCOCC.O=[N+]([O-])c1nc(Br)ccc1O>>CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-] | BrC1=NC(=C(C=C1)O)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].CCOCC>>BrC1=CC=C(C(=N1)[N+](=O)[O-])OCC(=O)OCC | C(O[CH2:2][CH3:1])[CH3:6].[OH:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]1[N+:15](=[O:16])[O-:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]1[N+:15](=[O:16])[O-:17] | CCOCC.O=[N+]([O-])c1nc(Br)ccc1O | CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-] | null | BrCC(=O)OCC | CC(=O)C | Acylation | OtherReaction | 93235095ed013a545ed42057f29dfe7f5561f72d80c5f9ee196c3c3abbd5e217 | e631da849ef77beac2d347b14b0af45e91e172bce5709654eb3b64211e5e4963 | c1ccncc1 | [#7;+:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7].[C;D1;H3:8]-[CH2;D2;+0:9]-O-C-[CH3;D1;+0:10]>>[#7;+:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[CH2;D2;+0:9]-[C;D1;H3:8]):[c:7] | 89 | [{"value": 89.0, "product": "BrC1=CC=C(C(=N1)[N+](=O)[O-])OCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-5-hydroxy-6-nitropyridine (30 g, 0.14 mole) was suspended in acetone (200 ml), and potassium carbonate (39 g, 0.28 mole) was added, followed by ethyl bromoacetate (15.7 ml, 0.14 mmole). The reaction was heated at reflux for 10 hr, then was cooled to room temperature and diluted with Et2O. The precipitate was re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ester.Ether | null | null | c1ccncc1 | HO- | BrCC(=O)OCC.CC(=O)C | null | null | CCOCC.O=[N+]([O-])c1nc(Br)ccc1O>BrCC(=O)OCC.CC(=O)C>CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c84d62cf667e4481a9079100f572ac2e | CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-]>>O=C1COc2ccc(Br)nc2N1 | BrC1=CC=C(C(=N1)[N+](=O)[O-])OCC(=O)OCC>>BrC=1C=CC=2OCC(NC2N1)=O | CCO[C:2](=[O:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[n:10][c:11]1[N+:12](=O)[O-]>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[n:10][c:11]2[NH:12]1 | CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-] | O=C1COc2ccc(Br)nc2N1 | null | [Fe] | CC(=O)O.CCOC(=O)C | Functional Group Interconversion | OtherReaction | 8ca06d4bb9b8192d0651eaee3df48d2ce53540bcc84755fa2392ddb4bb2e7134 | 42f24d3b25bb26f4d7fac0ebbebf6d046ea37d400eb2e6f47c39069d069d5e9d | O=C1COc2cccnc2N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[c:5]:[c:6](-[N+;H0;D3:7](=O)-[O-]):[#7;a:8]:[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[#8:4]-[c:5]:[c:6](:[#7;a:8]:[c:9])-[NH;D2;+0:7]-1 | null | [] | 90 | CELSIUS | null | null | Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90° C. for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Secondary amide | null | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | HO- | [Fe].CC(=O)O.CCOC(=O)C | 90 | null | CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-]>[Fe].CC(=O)O.CCOC(=O)C>O=C1COc2ccc(Br)nc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d22dafbc8fa14556bfe17a741ced1131 | O=C1COc2ccc(Br)nc2N1.OB(O)/C=C/c1ccccc1>>O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 | BrC=1C=CC=2OCC(NC2N1)=O.C1(=CC=CC=C1)/C=C/B(O)O.C([O-])([O-])=O.[K+].[K+]>>C(=C\C1=CC=CC=C1)/C=1C=CC=2OCC(NC2N1)=O | Br[c:8]1[cH:7][cH:6][c:5]2[c:18]([n:17]1)[NH:19][C:2](=[O:1])[CH2:3][O:4]2.OB(O)/[CH:9]=[CH:10]/[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][c:18]2[NH:19]1 | O=C1COc2ccc(Br)nc2N1.OB(O)/C=C/c1ccccc1 | O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.O.CCOC(=O)C | C-C Coupling | Suzuki coupling with boronic acids | 78d8ad3441f90b689fe1e4594cfb21db4fe84d29bf0173beafcec322882a7de6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].O-B(-O)/[CH;D2;+0:7]=[C:8]/[c:9](:[c:10]):[c:11]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](/[CH;D2;+0:7]=[C:8]/[c:9](:[c:10]):[c:11]):[c:5]:[c:6] | 38 | [{"value": 38.0, "product": "C(=C\\C1=CC=CC=C1)/C=1C=CC=2OCC(NC2N1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.7, "product": "C(=C\\C1=CC=CC=C1)/C=1C=CC=2OCC(NC2N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.O.CCOC(=O)C | null | null | O=C1COc2ccc(Br)nc2N1.OB(O)/C=C/c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.O.CCOC(=O)C>O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-877c28ca71f04fb4b49300ed1d05bc24 | N.O=c1cc(CO)occ1OCc1ccccc1>>O=c1cc(CO)[nH]cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC=1C(C=C(OC1)CO)=O.C1=C(OC=C(C1=O)O)CO.N.COC1=CC=CC=C1OC(CO)C(C2=CC(=C(C=C2)O)OC)O>>C(C1=CC=CC=C1)OC=1C(C=C(NC1)CO)=O | [NH3:7].o1[c:4]([CH2:5][OH:6])[cH:3][c:2](=[O:1])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:8]1>>[O:1]=[c:2]1[cH:3][c:4]([CH2:5][OH:6])[nH:7][cH:8][c:9]1[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | N.O=c1cc(CO)occ1OCc1ccccc1 | O=c1cc(CO)[nH]cc1OCc1ccccc1 | null | null | C(C)O | Miscellaneous | OtherReaction | a770a0f1322d1d6fc09ae7bc719fc50a835416dcc33e1a46a0f3709d69d63210 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1cc[nH]cc1OCc1ccccc1 | [#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6]-[O;D1;H1:7]):o:[cH;D2;+0:8]:1.[NH3;D0;+0:9]>>[#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6]-[O;D1;H1:7]):[nH;D2;+0:9]:[cH;D2;+0:8]:1 | null | [] | null | null | null | null | A mixture of 5-benzyloxy-2-hydroxymethyl-4-pyrone (prepared from Kojic acid by the method of D. Erol, J. Med. Chem., 1994, 29, 893) (9.7 g, 40 mmol), concentrated aqueous (880) ammonia (100 mL), and ethanol (20 mL) was heated to reflux overnight. The mixture was allowed to cool to room temperature then filtered. The re... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HO- | C(C)O | null | null | N.O=c1cc(CO)occ1OCc1ccccc1>C(C)O>O=c1cc(CO)[nH]cc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16b1af383eb34e43ae561786b9922520 | O=c1cc(CO)[nH]cc1OCc1ccccc1>>OCc1cc2c(cn1)OCCO2 | C([O-])([O-])=O.[K+].[K+].BrCCBr.C(C1=CC=CC=C1)OC=1C(C=C(NC1)CO)=O.[OH-].[Na+]>>O1CCOC=2C=NC(=CC21)CO | c1ccc(C[O:9][c:6]2[c:5](=[O:12])[cH:4][c:3]([CH2:2][OH:1])[nH:8][cH:7]2)cc1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][n:8]1)[O:9][CH2:10][CH2:11][O:12]2 | O=c1cc(CO)[nH]cc1OCc1ccccc1 | OCc1cc2c(cn1)OCCO2 | null | [Pd] | O.CN(C=O)C | Miscellaneous | OtherReaction | b6c1fc7b3260141cdca6ecdde0185e38f3d727f098f90d3c29d46e9d2a8df128 | 0b8c3604c907a509a420964c6ae7d48531f5f31bea2aa75832e44064b8fc58df | c1cc2c(cn1)OCCO2 | [C:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[c:6](-[O;H0;D2;+0:7]-C-c2:c:c:c:c:c:2):[c:8]:[nH;D2;+0:9]:1>>[C:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4]2:[c:6](:[c:8]:[n;H0;D2;+0:9]:1)-[O;H0;D2;+0:7]-[C:10]-[C:11]-[O;H0;D2;+0:5]-2 | null | [] | 85 | CELSIUS | null | null | A solution of 5-Benzyloxy-2-hydroxymethyl-1H-pyridin-4-one (2 g, 8.7 mmol) in water (220 mL) containing sodium hydroxide (17 mmol) was hydrogenated over 10% palladium on charcoal (1 g) for 4 hours. The mixture was filtered and evaporated to give a white solid. This solid was dissolved in N,N-dimethylformamide (8 mL) th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether.Ether | c1ccccc1.c1ccncc1 | c1cc2c(cn1)OCCO2 | c1cc2c(cn1)OCCO2 | Other | [Pd].O.CN(C=O)C | 85 | null | O=c1cc(CO)[nH]cc1OCc1ccccc1>[Pd].O.CN(C=O)C>OCc1cc2c(cn1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3abc7e042b3342a7a1acde5c8be8a44e | OCc1cc2c(cn1)OCCO2>>O=Cc1cc2c(cn1)OCCO2 | O1CCOC=2C=NC(=CC21)CO>>O1CCOC=2C=NC(=CC21)C=O | [OH:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][n:8]1)[O:9][CH2:10][CH2:11][O:12]2>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][n:8]1)[O:9][CH2:10][CH2:11][O:12]2 | OCc1cc2c(cn1)OCCO2 | O=Cc1cc2c(cn1)OCCO2 | null | [O-2].[O-2].[Mn+4] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cc2c(cn1)OCCO2 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 61 | [{"value": 61.0, "product": "O1CCOC=2C=NC(=CC21)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.6, "product": "O1CCOC=2C=NC(=CC21)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)-methanol (250 mg, 1.5 mmol) in dichloromethane (5 mL) was treated with manganese dioxide (650 mg, 7.5 mmol). After 3 days the mixture was filtered and evaporated affording a white solid (150 mg, 61%); MS (APCI+) m/z 166 (MH+).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cc2c(cn1)OCCO2 | null | [O-2].[O-2].[Mn+4].ClCCl | null | null | OCc1cc2c(cn1)OCCO2>[O-2].[O-2].[Mn+4].ClCCl>O=Cc1cc2c(cn1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c2b57db026d4b52aa151ef77a6cd671 | CC(C)(C)OC(=O)NCCN1CCNCC1.COc1ccc2ncc(F)c(Br)c2n1>>COc1ccc2ncc(F)c(N3CCN(CCNC(=O)OC(C)(C)C)CC3)c2n1 | BrC=1C(=CN=C2C=CC(=NC12)OC)F.N1(CCNCC1)CCNC(OC(C)(C)C)=O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C(=O)([O-])[O-].[Cs+].[Cs+]>>FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCNC(OC(C)(C)C)=O)OC | [NH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]1.Br[c:11]1[c:9]([F:10])[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:29][c:28]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([N:12]3[CH2:13][CH2:14][N:15]([CH2:16][... | CC(C)(C)OC(=O)NCCN1CCNCC1.COc1ccc2ncc(F)c(Br)c2n1 | COc1ccc2ncc(F)c(N3CCN(CCNC(=O)OC(C)(C)C)CC3)c2n1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 77ec5d86f504a3d28cd92b34f3de890922e3a4b6c38179297494772e0af34bc3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc2c(N3CCNCC3)ccnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3]:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]:[c:9]:1-[F;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[F;D1;H0:10]-[c:9]1:[c:8]:[#7;a:7]:[c:5](:[c:6]):[c:2](:[#7;a:3]:[c:4]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1 | 41.6 | [{"value": 41.0, "product": "FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCNC(OC(C)(C)C)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.6, "product": "FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCNC(OC(C)(C)C)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 15 | MINUTE | In a sealed tube, 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine (1.1 g, 4.3 mmol), 1,1-dimethylethyl [2-(1-piperazinyl)ethyl]carbamate (1 g, 4.3 mmol), Pd2dba3 (271 mg, 0.262 mmol), rac-Binap (163 mg, 0.262 mmol), Cs2CO3 (2.98 mg, 9.2 mmol) and 18-C-6 (115 mg, 0.436 mmol) in dioxane (22 mL) were combined and flushed... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1cnc2cccnc2c1 | c1cnc2cccnc2c1.C1C[NH]CC[NH]1 | c1cnc2cccnc2c1.C1C[NH]CC[NH]1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1 | 100 | 0.25 | CC(C)(C)OC(=O)NCCN1CCNCC1.COc1ccc2ncc(F)c(Br)c2n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1>COc1ccc2ncc(F)c(N3CCN(CCNC(=O)OC(C)(C)C)CC3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01c9682837ea4c8d9fe7904aabe24c3b | COc1ccc2ncc(F)c(N3CCN(CCNC(=O)OC(C)(C)C)CC3)c2n1>>COc1ccc2ncc(F)c(N3CCN(CCN)CC3)c2n1 | FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCNC(OC(C)(C)C)=O)OC.Cl.O1CCOCC1>>FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCN)OC | CC(C)(C)OC(=O)[NH:18][CH2:17][CH2:16][N:15]1[CH2:14][CH2:13][N:12]([c:11]2[c:9]([F:10])[cH:8][n:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[n:22][c:21]32)[CH2:20][CH2:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([N:12]3[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][NH2:18])[CH2:19][CH2:20]3)[c:21]2[n:2... | COc1ccc2ncc(F)c(N3CCN(CCNC(=O)OC(C)(C)C)CC3)c2n1 | COc1ccc2ncc(F)c(N3CCN(CCN)CC3)c2n1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cnc2c(N3CCNCC3)ccnc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 12 | HOUR | To a solution of 1,1-dimethylethyl (2-{4-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)carbamate (725 mg, 1.79 mmol) in MeOH (9 mL) at 25° C. was added dropwise a 4M solution of HCl in dioxane (3.1 mL, 12.53 mmol). After 12 h, the solution was concentrated the residue neutralized using excess MP ca... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cnc2cccnc2c1.C1C[NH]CC[NH]1 | HO- | CO | null | 12 | COc1ccc2ncc(F)c(N3CCN(CCNC(=O)OC(C)(C)C)CC3)c2n1>CO>COc1ccc2ncc(F)c(N3CCN(CCN)CC3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e315c8f4e184aab9984a7f0ddb67c6f | COc1ccc2ncc(F)c(N3CCN(CCN)CC3)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2>>COc1ccc2ncc(F)c(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)CC3)c2n1 | FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCN)OC.[O-]S(=O)(=O)[O-].[Na+].[Na+].O=C1NC2=C(SC1)C=CC(=N2)C=O.[BH4-].[Na+]>>FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([N:12]3[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][NH2:18])[CH2:31][CH2:32]3)[c:33]2[n:34]1.O=[CH:19][c:20]1[cH:21][cH:22][c:23]2[c:24]([n:25]1)[NH:26][C:27](=[O:28])[CH2:29][S:30]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([N:12]3... | COc1ccc2ncc(F)c(N3CCN(CCN)CC3)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2 | COc1ccc2ncc(F)c(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)CC3)c2n1 | null | null | C(Cl)Cl.CCO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CSc2ccc(CNCCN3CCN(c4ccnc5cccnc45)CC3)nc2N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8]-[C:7]):[c:3] | 30 | [{"value": 30.0, "product": "FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.7, "product": "FC=1C=NC2=CC=C(N=C2C1N1CCN(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of (2-{4-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)amine (155 mg, 0.508 mmol) in DCM-EtOH (5 mL, 1:1) were added Na2SO4 (144 mg, 1.02 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde (99 mg, 0.508 mmol). After 12 h at 25° C., the imine was quenched by addit... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2cccnc2c1.C1C[NH]CC[NH]1.c1cnc2c(c1)SCCN2 | Other | C(Cl)Cl.CCO | null | 12 | COc1ccc2ncc(F)c(N3CCN(CCN)CC3)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2>C(Cl)Cl.CCO>COc1ccc2ncc(F)c(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)CC3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac53345574d043ea8fa3e9e6e7420625 | CC(C)(C)OC(=O)NCCN1CCNC(=O)C1.COc1ccc2nccc(OS(=O)(=O)C(F)(F)F)c2n1>>COc1ccc2nccc(N3CCN(CCNC(=O)OC(C)(C)C)CC3=O)c2n1 | O=C1CN(CCN1)CCNC(OC(C)(C)C)=O.FC(S(=O)(=O)OC1=CC=NC2=CC=C(N=C12)OC)(F)F.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C(=O)([O-])[O-].[Cs+].[Cs+]>>COC=1N=C2C(=CC=NC2=CC1)N1C(CN(CC1)CCNC(OC(C)(C)C)=O)=O | [NH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C:26]1=[O:27].O=S(=O)(O[c:10]1[cH:9][cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:29][c:28]21)C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][N:14]([C... | CC(C)(C)OC(=O)NCCN1CCNC(=O)C1.COc1ccc2nccc(OS(=O)(=O)C(F)(F)F)c2n1 | COc1ccc2nccc(N3CCN(CCNC(=O)OC(C)(C)C)CC3=O)c2n1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | 006a4db21d86c71427ac99eb6a23e574b7017c5f62650c31fa4d5eda1f5fabd4 | e8f1037ddf00c3008e109a885e9239c96953665a705783a27060bdf402b979e6 | O=C1CNCCN1c1ccnc2cccnc12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[O;D1;H0:10]=[C:11]1-[C:12]-[#7:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[O;D1;H0:10]=[C:11]1-[C:12]-[#7:13]-[C:14]-[C:15]-[N;H0;D3;+0:16]-1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9] | 53.2 | [{"value": 53.0, "product": "COC=1N=C2C(=CC=NC2=CC1)N1C(CN(CC1)CCNC(OC(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "COC=1N=C2C(=CC=NC2=CC1)N1C(CN(CC1)CCNC(OC(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 15 | MINUTE | In a sealed tube 1,1-dimethylethyl [2-(3-oxo-1-piperazinyl)ethyl]carbamate (1.7 g, 7.02 mmol), 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (2.17 g, 7.02 mmol), Pd2dba3 (436 mg, 0.421 mmol), rac-Binap (262 mg, 0.421 mmol), Cs2CO3 (4.81 g, 14.75 mmol) and 18-C-6 (186 mg, 0.702 mmol) in dioxane (35 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Secondary amide | Tertiary amide | C1CNCC[NH]1.c1cnc2cccnc2c1 | c1cnc2cccnc2c1.C1C[NH]CC[NH]1 | c1cnc2cccnc2c1.C1C[NH]CC[NH]1 | TfOH.HO- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1 | 100 | 0.25 | CC(C)(C)OC(=O)NCCN1CCNC(=O)C1.COc1ccc2nccc(OS(=O)(=O)C(F)(F)F)c2n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1>COc1ccc2nccc(N3CCN(CCNC(=O)OC(C)(C)C)CC3=O)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8743ace4140543c696c4fc726ad687bf | COc1ccc2nccc(N3CCN(CCNC(=O)OC(C)(C)C)CC3=O)c2n1>>COc1ccc2nccc(N3CCN(CCN)CC3=O)c2n1 | COC=1N=C2C(=CC=NC2=CC1)N1C(CN(CC1)CCNC(OC(C)(C)C)=O)=O.Cl.O1CCOCC1>>NCCN1CC(N(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O | CC(C)(C)OC(=O)[NH:17][CH2:16][CH2:15][N:14]1[CH2:13][CH2:12][N:11]([c:10]2[cH:9][cH:8][n:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[n:22][c:21]32)[C:19](=[O:20])[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][NH2:17])[CH2:18][C:19]3=[O:20])[c:21]2[n:22]... | COc1ccc2nccc(N3CCN(CCNC(=O)OC(C)(C)C)CC3=O)c2n1 | COc1ccc2nccc(N3CCN(CCN)CC3=O)c2n1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CNCCN1c1ccnc2cccnc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 98 | [{"value": 98.0, "product": "NCCN1CC(N(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "NCCN1CC(N(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 1,1-dimethylethyl (2-{4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-3-oxo-1-piperazinyl}ethyl)carbamate (1.5 g, 3.74 mmol) in MeOH (19 mL) at 25° C. was added dropwise, a solution of HCl in dioxane (6.5 mL, 26.18 mmol, 4M HCl in dioxane). After 12 h, the solution was concentrated and the residue neutralized ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cnc2cccnc2c1.C1C[NH]CC[NH]1 | HO- | CO | null | 12 | COc1ccc2nccc(N3CCN(CCNC(=O)OC(C)(C)C)CC3=O)c2n1>CO>COc1ccc2nccc(N3CCN(CCN)CC3=O)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a65a00b0f8b44730a1bd2c38e6d40aed | COc1ccc2nccc(N3CCN(CCN)CC3=O)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2>>COc1ccc2nccc(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)CC3=O)c2n1 | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].NCCN1CC(N(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O.[O-]S(=O)(=O)[O-].[Na+].[Na+].O=C1NC2=C(SC1)C=CC(=N2)C=O>>COC=1N=C2C(=CC=NC2=CC1)N1C(CN(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][NH2:17])[CH2:30][C:31]3=[O:32])[c:33]2[n:34]1.O=[CH:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([n:24]1)[NH:25][C:26](=[O:27])[CH2:28][S:29]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][... | COc1ccc2nccc(N3CCN(CCN)CC3=O)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2 | COc1ccc2nccc(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)CC3=O)c2n1 | null | null | C(Cl)Cl.CCO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CSc2ccc(CNCCN3CCN(c4ccnc5cccnc45)C(=O)C3)nc2N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8]-[C:7]):[c:3] | 37.4 | [{"value": 37.0, "product": "COC=1N=C2C(=CC=NC2=CC1)N1C(CN(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.4, "product": "COC=1N=C2C(=CC=NC2=CC1)N1C(CN(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 4-(2-aminoethyl)-1-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-piperazinone (168 mg, 0.558 mmol) in DCM-EtOH (6 mL, 5:1) at 25° C. were added Na2SO4 (158 mg, 1.11 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde (108 mg, 0.558 mmol). After 12 h, Na(OAc)3BH (177 mg, 0.837 mmol) was a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2cccnc2c1.C1C[NH]CC[NH]1.c1cnc2c(c1)SCCN2 | Other | C(Cl)Cl.CCO | null | 12 | COc1ccc2nccc(N3CCN(CCN)CC3=O)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2>C(Cl)Cl.CCO>COc1ccc2nccc(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)CC3=O)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-671a451267fd4c81a29411df3da2926a | NN.O=C(CCl)N(CCN1C(=O)c2ccccc2C1=O)CCN1C(=O)c2ccccc2C1=O>>O=C1CNCCN1CCN1C(=O)c2ccccc2C1=O | ClCC(=O)N(CCN1C(C2=CC=CC=C2C1=O)=O)CCN1C(C2=CC=CC=C2C1=O)=O.O.NN>>O=C1N(CCNC1)CCN1C(C2=CC=CC=C2C1=O)=O | N[NH2:4].O=C1c2ccccc2C(=O)N1[CH2:5][CH2:6][N:7]([C:2](=[O:1])[CH2:3]Cl)[CH2:8][CH2:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[O:20]>>[O:1]=[C:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[O:20] | NN.O=C(CCl)N(CCN1C(=O)c2ccccc2C1=O)CCN1C(=O)c2ccccc2C1=O | O=C1CNCCN1CCN1C(=O)c2ccccc2C1=O | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | f87e90e48bf3e9d6b1521a09860944dacb333a920b3ae665c6830122132042af | eeeba999b5c92a53a7b03319e7f244542ac4ff6e37f88b8caae2b0a59717f721 | O=C1CNCCN1CCN1C(=O)c2ccccc2C1=O | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6]-[CH2;D2;+0:7]-N1-C(=O)-c2:c:c:c:c:c:2-C-1=O.N-[NH2;D1;+0:8]>>[C:5]-[#7:4]1-[C:6]-[CH2;D2;+0:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-1=[O;D1;H0:3] | 34.4 | [{"value": 34.0, "product": "O=C1N(CCNC1)CCN1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.4, "product": "O=C1N(CCNC1)CCN1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 2-chloro-N,N-bis[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]acetamide (2 g, 4.55 mmol) in EtOH (230 mL) was added hydrazine hydrate (213 μL, 6.83 mmol). After 12 h at 85° C., the solution was concentrated and the residue purified via column chromatography (silica, 3% MeOH in DCM (1% NH4OH)) yieldi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Substituted dicarboximide | Secondary amine | c1ccc2c(c1)CNC2 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccc2c(c1)C[NH]C2 | HCl | CCO | null | 12 | NN.O=C(CCl)N(CCN1C(=O)c2ccccc2C1=O)CCN1C(=O)c2ccccc2C1=O>CCO>O=C1CNCCN1CCN1C(=O)c2ccccc2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a4f0297f0af44dbb58c5d7903615c4b | COc1ccc2nccc(N3CCN(CCN4Cc5ccccc5C4)C(=O)C3)c2n1>>COc1ccc2nccc(N3CCN(CCN)C(=O)C3)c2n1 | COC=1N=C2C(=CC=NC2=CC1)N1CC(N(CC1)CCN1CC2=CC=CC=C2C1)=O.O.NN>>NCCN1C(CN(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O | c1ccc2c(c1)C[N:17]([CH2:16][CH2:15][N:14]1[CH2:13][CH2:12][N:11]([c:10]3[cH:9][cH:8][n:7][c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[n:22][c:21]43)[CH2:20][C:18]1=[O:19])C2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][NH2:17])[C:18](=[O:19])[CH2:20]3)[c:21]2[n:22... | COc1ccc2nccc(N3CCN(CCN4Cc5ccccc5C4)C(=O)C3)c2n1 | COc1ccc2nccc(N3CCN(CCN)C(=O)C3)c2n1 | null | null | CCO | Deprotection | OtherReaction | 45767f922371b06f53f6df95a46b2076e8596bdab18e195f41115c6c9a29410c | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | O=C1CN(c2ccnc3cccnc23)CCN1 | [C:1]-[C:2]-[N;H0;D3;+0:3]1-C-c2:c:c:c:c:c:2-C-1>>[C:1]-[C:2]-[NH2;D1;+0:3] | 66 | [{"value": 66.0, "product": "NCCN1C(CN(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "NCCN1C(CN(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-(2-{4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-oxo-1-piperazinyl}ethyl)-1H-isoindole-1,3(2H-dione (100 mg, 0.232 mmol) in EtOH (2 mL) was added hydrazine hydrate (120 μL, 3.85 mmol). After 2 h at 85° C., the solution was concentrated and the residue purified by column chromatography (silica, 5-10% MeO... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1cnc2cccnc2c1.C1C[NH]CC[NH]1 | Other | CCO | null | 2 | COc1ccc2nccc(N3CCN(CCN4Cc5ccccc5C4)C(=O)C3)c2n1>CCO>COc1ccc2nccc(N3CCN(CCN)C(=O)C3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ae3b251d7e34edebd37796d5fde55d4 | COc1ccc2nccc(N3CCN(CCN)C(=O)C3)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2>>COc1ccc2nccc(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)C(=O)C3)c2n1 | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].NCCN1C(CN(CC1)C1=CC=NC2=CC=C(N=C12)OC)=O.C(=O)(O)[O-].[Na+].O=C1NC2=C(SC1)C=CC(=N2)C=O>>COC=1N=C2C(=CC=NC2=CC1)N1CC(N(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][NH2:17])[C:30](=[O:31])[CH2:32]3)[c:33]2[n:34]1.O=[CH:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([n:24]1)[NH:25][C:26](=[O:27])[CH2:28][S:29]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12... | COc1ccc2nccc(N3CCN(CCN)C(=O)C3)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2 | COc1ccc2nccc(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)C(=O)C3)c2n1 | null | null | C(Cl)Cl.CCO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1CSc2ccc(CNCCN3CCN(c4ccnc5cccnc45)CC3=O)nc2N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8]-[C:7]):[c:3] | 67 | [{"value": 67.0, "product": "COC=1N=C2C(=CC=NC2=CC1)N1CC(N(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "COC=1N=C2C(=CC=NC2=CC1)N1CC(N(CC1)CCNCC=1C=CC=2SCC(NC2N1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 1-(2-aminoethyl)-4-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-piperazinone (46 mg, 0.15 mmol) in DCM-EtOH (2 mL, 1:1) were added NaHCO3 (32 mg, 0.38 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde (29 mg, 0.15 mmol). After 12 h, NaBH(OAc)3 (38 mg, 0.15 mmol) was added. After an ad... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cnc2cccnc2c1.C1C[NH]CC[NH]1.c1cnc2c(c1)SCCN2 | Other | C(Cl)Cl.CCO | null | 12 | COc1ccc2nccc(N3CCN(CCN)C(=O)C3)c2n1.O=Cc1ccc2c(n1)NC(=O)CS2>C(Cl)Cl.CCO>COc1ccc2nccc(N3CCN(CCNCc4ccc5c(n4)NC(=O)CS5)C(=O)C3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a984ce51f9a42a5a39c8a3b290d96d1 | CC(C)(C)OC(=O)NCCC1CCNCC1.COc1ccc2ncc(F)c(Br)c2c1.O=Cc1ccc2c(n1)NC(=O)CO2>>COc1ccc2ncc(F)c(N3CCC(CCNCc4ccc5c(n4)NC(=O)CO5)CC3)c2c1 | BrC=1C(=CN=C2C=CC(=NC12)OC)F.O=C1NC2=C(SC1)C=CC(=N2)C=O.N1CCC(CC1)CCNC(OC(C)(C)C)=O.N1(CCNCC1)CCNC(OC(C)(C)C)=O.O=C1NC2=C(OC1)C=CC(=N2)C=O.BrC1=C(C=NC2=CC=C(C=C12)OC)F>>FC=1C=NC2=CC=C(C=C2C1N1CCC(CC1)CCNCC=1C=CC=2OCC(NC2N1)=O)OC | CC(C)(C)OC(=O)[NH:18][CH2:17][CH2:16][CH:15]1[CH2:14][CH2:13][NH:12][CH2:32][CH2:31]1.Br[c:11]1[c:9]([F:10])[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][c:33]21.O=[CH:19][c:20]1[cH:21][cH:22][c:23]2[c:24]([n:25]1)[NH:26][C:27](=[O:28])[CH2:29][O:30]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([F:1... | CC(C)(C)OC(=O)NCCC1CCNCC1.COc1ccc2ncc(F)c(Br)c2c1.O=Cc1ccc2c(n1)NC(=O)CO2 | COc1ccc2ncc(F)c(N3CCC(CCNCc4ccc5c(n4)NC(=O)CO5)CC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d6ce8e2701dac5bb6260286b87f14a893e167f05790ce0db6a6e461400782ef6 | 86932104f2b0880ba2f4854cdbfacf6a9b39f91eb4e2846379a6a2e1f6085b10 | O=C1COc2ccc(CNCCC3CCN(c4ccnc5ccccc45)CC3)nc2N1 | Br-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[F;D1;H0:9].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:10]-[C:11]-[C:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17].O=[CH;D2;+0:18]-[c:19](:[c:20]):[#7;a:21]:[c:22]-[#7:23]>>[#7:23]-[c:22]:[#7;a:21]:[c:19](-[CH2;D2;+0:18]-[NH;D2;+0:10]-[C:11]-[C:12]):[c:20].[C:13]... | 33 | [{"value": 33.0, "product": "FC=1C=NC2=CC=C(C=C2C1N1CCC(CC1)CCNCC=1C=CC=2OCC(NC2N1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.7, "product": "FC=1C=NC2=CC=C(C=C2C1N1CCC(CC1)CCNCC=1C=CC=2OCC(NC2N1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (100 mg, 33%) was prepared as a yellow solid according to Example 1, except substituting the following three reagents: 1,1-dimethylethyl [2-(4-piperidinyl)ethyl]carbamate (1 g, 4.38 mmol) [prepared according to Ambler, J.; et. al. Bioorg. Med. Chem. Lett. 1999, 9, 9, 1317.] for 1,1-dimethylethyl [2-(... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1CC[NH]CC1 | c1ccc2ncccc2c1.C1CC[NH]CC1.c1cnc2c(c1)OCCN2 | HBr | null | null | null | CC(C)(C)OC(=O)NCCC1CCNCC1.COc1ccc2ncc(F)c(Br)c2c1.O=Cc1ccc2c(n1)NC(=O)CO2>>COc1ccc2ncc(F)c(N3CCC(CCNCc4ccc5c(n4)NC(=O)CO5)CC3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b00dbf4c77824248b309f19951c6afa3 | CCOC(=O)CC1(O)CCN(Cc2ccccc2)CC1.N>>NC(=O)CC1(O)CCN(Cc2ccccc2)CC1 | OC1(CCN(CC1)CC1=CC=CC=C1)CC(=O)OCC.N.CO>>OC1(CCN(CC1)CC1=CC=CC=C1)CC(=O)N | CCO[C:2](=[O:3])[CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1.[NH3:1]>>[NH2:1][C:2](=[O:3])[CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1 | CCOC(=O)CC1(O)CCN(Cc2ccccc2)CC1.N | NC(=O)CC1(O)CCN(Cc2ccccc2)CC1 | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc(CN2CCCCC2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH3;D0;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | null | [] | null | null | null | null | A solution of ethyl [4-hydroxy-1-(phenylmethyl)-4-piperidinyl]acetate (15 g, 54.15 mmol) [prepared according to Caroon, J. M.; et al. J. Med. Chem. 1981, 24,1320.] in 7N NH3-MeOH (16 mL) was heated to 100° C. in a sealed tube for 3d. The solution was cooled and concentrated and the residue washed with DCM providing the... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CC[NH]CC1.c1ccccc1 | HO- | null | null | null | CCOC(=O)CC1(O)CCN(Cc2ccccc2)CC1.N>>NC(=O)CC1(O)CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d6298efaa5e43d792fd28026cd8487b | NC(=O)CC1(O)CCN(Cc2ccccc2)CC1>>NCCC1(O)CCN(Cc2ccccc2)CC1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].OC1(CCN(CC1)CC1=CC=CC=C1)CC(=O)N>>NCCC1(CCN(CC1)CC1=CC=CC=C1)O | O=[C:2]([NH2:1])[CH2:3][C:4]1([OH:5])[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[NH2:1][CH2:2][CH2:3][C:4]1([OH:5])[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | NC(=O)CC1(O)CCN(Cc2ccccc2)CC1 | NCCC1(O)CCN(Cc2ccccc2)CC1 | null | null | C1CCOC1 | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccc(CN2CCCCC2)cc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[N;D1;H2:2] | null | [] | 25 | CELSIUS | null | null | To a solution of LiAlH4 (1.8 g, 0.048 mmol) in THF (40 mL) at 0° C. was added dropwise via addition funnel a solution of 2-[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]acetamide (4 g, 0.016 mmol) in THF (40 mL). The solution warmed to 25° C. and was then heated to reflux for 12 h. After cooling, the solution was then care... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | C1CC[NH]CC1.c1ccccc1 | Other | C1CCOC1 | 25 | null | NC(=O)CC1(O)CCN(Cc2ccccc2)CC1>C1CCOC1>NCCC1(O)CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6d06e660fca422daa7b9cf5d93d7abb | CC(C)(C)OC(=O)NCCC1(O)CCN(Cc2ccccc2)CC1>>CC(C)(C)OC(=O)NCCC1(O)CCNCC1 | OC1(CCN(CC1)CC1=CC=CC=C1)CCNC(OC(C)(C)C)=O>>OC1(CCNCC1)CCNC(OC(C)(C)C)=O | c1ccc(C[N:15]2[CH2:14][CH2:13][C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([OH:12])[CH2:17][CH2:16]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1([OH:12])[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | CC(C)(C)OC(=O)NCCC1(O)CCN(Cc2ccccc2)CC1 | CC(C)(C)OC(=O)NCCC1(O)CCNCC1 | null | [OH-].[OH-].[Pd+2] | CCO | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 100.4 | [{"value": 100.4, "product": "OC1(CCNCC1)CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of 1,1-dimethylethyl {2-[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]ethyl}carbamate (3.2 g, 9.5 mmol) and Pd(OH)2 (1.92 g, 60 wt %) in EtOH (50 mL) was hydrogenated using a Parr Shaker under 50 psi. After 12 h, the solution was filtered through Celite® and concentrated yielding the title compound (2.33 g, quan... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | Other | [OH-].[OH-].[Pd+2].CCO | null | 12 | CC(C)(C)OC(=O)NCCC1(O)CCN(Cc2ccccc2)CC1>[OH-].[OH-].[Pd+2].CCO>CC(C)(C)OC(=O)NCCC1(O)CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ce3a00dab6444358b2c2894e3b68f80 | CC(C)(C)OC(=O)NCCC1(O)CCNCC1.COc1ccc2ncc(F)c(Br)c2c1.O=Cc1ccc2c(n1)NC(=O)CO2>>COc1ccc2ncc(F)c(N3CCC(O)(CCNCc4ccc5c(n4)NC(=O)CO5)CC3)c2c1 | BrC=1C(=CN=C2C=CC(=NC12)OC)F.O=C1NC2=C(SC1)C=CC(=N2)C=O.OC1(CCNCC1)CCNC(OC(C)(C)C)=O.N1(CCNCC1)CCNC(OC(C)(C)C)=O.O=C1NC2=C(OC1)C=CC(=N2)C=O.BrC1=C(C=NC2=CC=C(C=C12)OC)F>>FC=1C=NC2=CC=C(C=C2C1N1CCC(CC1)(O)CCNCC=1C=CC=2OCC(NC2N1)=O)OC | CC(C)(C)OC(=O)[NH:19][CH2:18][CH2:17][C:15]1([OH:16])[CH2:14][CH2:13][NH:12][CH2:33][CH2:32]1.Br[c:11]1[c:9]([F:10])[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][c:34]21.O=[CH:20][c:21]1[cH:22][cH:23][c:24]2[c:25]([n:26]1)[NH:27][C:28](=[O:29])[CH2:30][O:31]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c... | CC(C)(C)OC(=O)NCCC1(O)CCNCC1.COc1ccc2ncc(F)c(Br)c2c1.O=Cc1ccc2c(n1)NC(=O)CO2 | COc1ccc2ncc(F)c(N3CCC(O)(CCNCc4ccc5c(n4)NC(=O)CO5)CC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d6ce8e2701dac5bb6260286b87f14a893e167f05790ce0db6a6e461400782ef6 | 86932104f2b0880ba2f4854cdbfacf6a9b39f91eb4e2846379a6a2e1f6085b10 | O=C1COc2ccc(CNCCC3CCN(c4ccnc5ccccc45)CC3)nc2N1 | Br-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[F;D1;H0:9].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:10]-[C:11]-[C:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17].O=[CH;D2;+0:18]-[c:19](:[c:20]):[#7;a:21]:[c:22]-[#7:23]>>[#7:23]-[c:22]:[#7;a:21]:[c:19](-[CH2;D2;+0:18]-[NH;D2;+0:10]-[C:11]-[C:12]):[c:20].[C:13]... | 26.1 | [{"value": 26.0, "product": "FC=1C=NC2=CC=C(C=C2C1N1CCC(CC1)(O)CCNCC=1C=CC=2OCC(NC2N1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.1, "product": "FC=1C=NC2=CC=C(C=C2C1N1CCC(CC1)(O)CCNCC=1C=CC=2OCC(NC2N1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (71 mg, 26%) was prepared as a yellow solid according to Example 1, except substituting the following three reagents: 1,1-dimethylethyl [2-(4-hydroxy-4-piperidinyl)ethyl]carbamate (1.5 g, 6.15 mmol) [prepared according to Example 20] for 1,1-dimethylethyl [2-(1-piperazinyl)ethyl]carbamate, 4-bromo-3-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1CC[NH]CC1 | c1ccc2ncccc2c1.C1CC[NH]CC1.c1cnc2c(c1)OCCN2 | HBr | null | null | null | CC(C)(C)OC(=O)NCCC1(O)CCNCC1.COc1ccc2ncc(F)c(Br)c2c1.O=Cc1ccc2c(n1)NC(=O)CO2>>COc1ccc2ncc(F)c(N3CCC(O)(CCNCc4ccc5c(n4)NC(=O)CO5)CC3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de5b0b3700db4aca811d49ebfe56129e | C[CH2][Al]([C]#N)[CH2]C.O=CC1CCN(Cc2ccccc2)CC1>>N#CC(O)C1CCN(Cc2ccccc2)CC1 | C1(=CC=CC=C1)CN1CCC(CC1)C=O.[Al](CC)(CC)C#N>>OC(C#N)C1CCN(CC1)CC1=CC=CC=C1 | C[CH2][Al]([CH2]C)[C:2]#[N:1].[CH:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[N:1]#[C:2][CH:3]([OH:4])[CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | C[CH2][Al]([C]#N)[CH2]C.O=CC1CCN(Cc2ccccc2)CC1 | N#CC(O)C1CCN(Cc2ccccc2)CC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 8c041e359859f706dea3df6c569856baae4527da3f93ef77c87a78699d1f1de1 | 27f17102d7f18741d48a0b424bdba8e529f610a2430bc44475fa64f36b2c62ae | c1ccc(CN2CCCCC2)cc1 | C-[CH2]-[Al](-[C;H0;D2;+0:1]#[N;D1;H0:2])-[CH2]-C.[C:3]-[C:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6])-[C:7]>>[C:3]-[C:4](-[CH;D3;+0:5](-[OH;D1;+0:6])-[C;H0;D2;+0:1]#[N;D1;H0:2])-[C:7] | null | [] | null | null | 1 | HOUR | To a solution of 1-(phenylmethyl)-4-piperidinecarbaldehyde (2.35 g, 11.6 mmol)[prepared according to Alfaro-Lopez, J.; et al. J. Med. Chem. 1999, 42, 5359] in THF (160 mL) at 0° C. was added dropwise Et2AlCN (25 mL, 1 M solution in toluene). After 1 h, the solution was partitioned between NaHCO3(sat)-DCM. The aqueous p... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile | Nitrile.Secondary alcohol | null | null | C1CC[NH]CC1.c1ccccc1 | Other | C1CCOC1 | null | 1 | C[CH2][Al]([C]#N)[CH2]C.O=CC1CCN(Cc2ccccc2)CC1>C1CCOC1>N#CC(O)C1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1a82202107b4eb58f667246f28292f6 | N#CC(O)C1CCN(Cc2ccccc2)CC1>>NCC(O)C1CCN(Cc2ccccc2)CC1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].OC(C#N)C1CCN(CC1)CC1=CC=CC=C1>>NCC(O)C1CCN(CC1)CC1=CC=CC=C1 | [N:1]#[C:2][CH:3]([OH:4])[CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[NH2:1][CH2:2][CH:3]([OH:4])[CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | N#CC(O)C1CCN(Cc2ccccc2)CC1 | NCC(O)C1CCN(Cc2ccccc2)CC1 | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(CN2CCCCC2)cc1 | [C:1]-[C:2](-[O;D1;H1:3])-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[C:1]-[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | null | null | 12 | HOUR | To a solution of LiAlH4 (1.1 g, 28.7 mmol) in THF (25 mL) at 0° C. was added dropwise via addition funnel a solution of hydroxy[1-(phenylmethyl)-4-piperidinyl]acetonitrile (2.2 g, 9.56 mmol) in THF (25 mL). After 12 h at 25° C., the solution was carefully quenched by dropwise additional of sodium potassium tartrate and... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1 | null | C1CCOC1 | null | 12 | N#CC(O)C1CCN(Cc2ccccc2)CC1>C1CCOC1>NCC(O)C1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e154ecf8e6941e7824d1b43eee168f3 | CC(C)(C)OC(=O)NCC(O)C1CCN(Cc2ccccc2)CC1>>CC(C)(C)OC(=O)NCC(O)C1CCNCC1 | OC(CNC(OC(C)(C)C)=O)C1CCN(CC1)CC1=CC=CC=C1>>OC(CNC(OC(C)(C)C)=O)C1CCNCC1 | c1ccc(C[N:15]2[CH2:14][CH2:13][CH:12]([CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[OH:11])[CH2:17][CH2:16]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([OH:11])[CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | CC(C)(C)OC(=O)NCC(O)C1CCN(Cc2ccccc2)CC1 | CC(C)(C)OC(=O)NCC(O)C1CCNCC1 | null | [OH-].[OH-].[Pd+2] | null | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | 12 | HOUR | A solution of 1,1-dimethylethyl {2-hydroxy-2-[1-(phenylmethyl)-4-piperidinyl]ethyl}carbamate (2 g, 5.97 mmol) and Pd(OH)2 (1.2 g, 60 wt %) in ETOH (30 mL) was hydrogenated at 60 psi using a Parr Shaker. After 12 h, the solution was filtered through Celite® and concentrated affording the title compound as a yellow oil w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | Other | [OH-].[OH-].[Pd+2] | null | 12 | CC(C)(C)OC(=O)NCC(O)C1CCN(Cc2ccccc2)CC1>[OH-].[OH-].[Pd+2]>CC(C)(C)OC(=O)NCC(O)C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62e1a56f9c2d4da692d9cff1587c1dbf | CC(O)c1cccc([N+](=O)[O-])c1.II>>O=[N+]([O-])c1cccc(CCI)c1 | II.[N+](=O)([O-])C=1C=C(C=CC1)C(C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1.[Cl-].[NH4+]>>ICCC1=CC(=CC=C1)[N+](=O)[O-] | O[CH:9]([c:8]1[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:12]1)[CH3:10].I[I:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][CH2:10][I:11])[cH:12]1 | CC(O)c1cccc([N+](=O)[O-])c1.II | O=[N+]([O-])c1cccc(CCI)c1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | a745186183d4a15b59814e6fc4c3c1771ba75d7b6cb6013938f3291359933c57 | c91da83995689026557e85e5b7af4b62e49c5d2540babd4bfd2bac63108f59c6 | c1ccccc1 | I-[I;H0;D1;+0:1].O-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[I;H0;D1;+0:1]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[c:4](:[c:5]):[c:6] | 90.6 | [{"value": 90.6, "product": "ICCC1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 5 g of 3-nitrophenylethanol, 9.4 g of triphenylphosphine and 3.1 g of imidazole are dissolved in 250 ml of THF, mixed in portions with 9.1 g of iodine and stirred for 15 hours at room temperature. The reaction mixture is mixed with ammonium chloride solution and extracted with dichloromethane. The organic phase is wash... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Primary halide | null | null | c1ccccc1 | HI | C1CCOC1 | null | 15 | CC(O)c1cccc([N+](=O)[O-])c1.II>C1CCOC1>O=[N+]([O-])c1cccc(CCI)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20931d4c8bc648dea128a75c22c23fa2 | CC(O)c1ccc([N+](=O)[O-])cc1.II>>O=[N+]([O-])c1ccc(CCI)cc1 | II.[N+](=O)([O-])C1=CC=C(C=C1)C(C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1.[Cl-].[NH4+]>>ICCC1=CC=C(C=C1)[N+](=O)[O-] | O[CH:8]([c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:12][cH:11]1)[CH3:9].I[I:10]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][I:10])[cH:11][cH:12]1 | CC(O)c1ccc([N+](=O)[O-])cc1.II | O=[N+]([O-])c1ccc(CCI)cc1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | a745186183d4a15b59814e6fc4c3c1771ba75d7b6cb6013938f3291359933c57 | c91da83995689026557e85e5b7af4b62e49c5d2540babd4bfd2bac63108f59c6 | c1ccccc1 | I-[I;H0;D1;+0:1].O-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[I;H0;D1;+0:1]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[c:4](:[c:5]):[c:6] | 93.4 | [{"value": 93.4, "product": "ICCC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 15 g of 4-nitrophenylethanol, 28.1 g of triphenylphosphine and 9.2 g of imidazole are dissolved in 500 ml of THF, mixed in portions with 27.77 g of iodine and stirred for 2 hours at room temperature. The reaction mixture is mixed with ammonium chloride solution and extracted with dichloromethane. The organic phase is w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Primary halide | null | null | c1ccccc1 | HI | C1CCOC1 | null | 2 | CC(O)c1ccc([N+](=O)[O-])cc1.II>C1CCOC1>O=[N+]([O-])c1ccc(CCI)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a93efac43ae64714959bf862a476e87d | NCCCN1CCCC1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(NCCCN1CCCC1)c1cccc([N+](=O)[O-])c1 | C([O-])(O)=O.[Na+].NCCCN1CCCC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1>>[N+](=O)([O-])C=1C=C(C(=O)NCCCN2CCCC2)C=CC1 | [NH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.O[C:2](=[O:1])[c:12]1[cH:13][cH:14][c:16]([N+:17](=[O:18])[O-:19])[cH:15][cH:20]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | NCCCN1CCCC1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(NCCCN1CCCC1)c1cccc([N+](=O)[O-])c1 | null | null | C(C)N(CC)CC.CN(C=O)C | Acylation | OtherReaction | 9d25d98f59135768d101893aea29d6387a3faacd3c3dd50a18ac091ea3c662aa | da1b488149e38a29693c43ee5f9b639c8cbea1cf36bd400f77445e2873a25464 | O=C(NCCCN1CCCC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:1.[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:10]:[c;H0;D3;+0:6](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]... | 67.9 | [{"value": 67.9, "product": "[N+](=O)([O-])C=1C=C(C(=O)NCCCN2CCCC2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 500 mg of 4-nitrobenzoic acid is dissolved in 20 ml of dimethylformamide, mixed with 370 μl of triethylamine, 342 mg of N-(3-aminopropyl)-pyrrolidine and 866 mg TBTU, and stirred for 20 hours at room temperature. The reaction mixture is mixed with semi-saturated sodium bicarbonate solution and extracted with dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group.Primary amine | Nitro group.Secondary amide | c1ccccc1 | c1ccccc1 | C1CC[NH]C1.c1ccccc1 | HO- | C(C)N(CC)CC.CN(C=O)C | null | 20 | NCCCN1CCCC1.O=C(O)c1ccc([N+](=O)[O-])cc1>C(C)N(CC)CC.CN(C=O)C>O=C(NCCCN1CCCC1)c1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f379d549df843f0bbefe14fa3bf253a | COCCOCC(=O)O.Nc1cccc([N+](=O)[O-])c1>>COCCOCC(=O)Nc1cccc([N+](=O)[O-])c1 | C([O-])(O)=O.[Na+].COCCOCC(=O)O.ClC(=O)OCC(C)C.[N+](=O)([O-])C=1C=C(N)C=CC1>>COCCOCC(=O)NC1=CC(=CC=C1)[N+](=O)[O-] | O[C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | COCCOCC(=O)O.Nc1cccc([N+](=O)[O-])c1 | COCCOCC(=O)Nc1cccc([N+](=O)[O-])c1 | null | null | O1CCCC1.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 81.5 | [{"value": 81.5, "product": "COCCOCC(=O)NC1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 5 g of (2-methoxyethoxy)-acetic acid is dissolved in 500 ml of tetrahydrofuran. 9.7 ml of triethylamine and 5.6 ml of isobutyl chloroformate are added at 0° C., and it is stirred for 30 minutes at 0° C. 5.0 g of 3-nitroaniline is added, and it is stirred for another 15 hours at room temperature. The reaction mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O1CCCC1.C(C)N(CC)CC | 0 | 0.5 | COCCOCC(=O)O.Nc1cccc([N+](=O)[O-])c1>O1CCCC1.C(C)N(CC)CC>COCCOCC(=O)Nc1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1dda6433de5b4aab9845db9fde330951 | COCCOCC(=O)O.Nc1cccc(N)n1>>COCCOCC(=O)Nc1cccc(N)n1 | C([O-])(O)=O.[Na+].COCCOCC(=O)O.ClC(=O)OCC(C)C.NC1=NC(=CC=C1)N>>NC1=CC=CC(=N1)NC(COCCOC)=O | O[C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH2:15])[n:16]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH2:15])[n:16]1 | COCCOCC(=O)O.Nc1cccc(N)n1 | COCCOCC(=O)Nc1cccc(N)n1 | null | null | O1CCCC1.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | 0 | CELSIUS | 30 | MINUTE | 4.9 ml of (2-methoxyethoxy)-acetic acid is dissolved in 500 ml of tetrahydrofuran. 9.7 ml of triethylamine and 5.6 ml of isobutyl chloroformate are added at 0° C., and it is stirred for 30 minutes at 0° C. 3.96 g of 2,6-diaminopyridine is added, and it is stirred for another 4 hours at room temperature. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | O1CCCC1.C(C)N(CC)CC | 0 | 0.5 | COCCOCC(=O)O.Nc1cccc(N)n1>O1CCCC1.C(C)N(CC)CC>COCCOCC(=O)Nc1cccc(N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bedb66c7b8484f62b316284fd071bd58 | O=C(CBr)c1cccc([N+](=O)[O-])c1>>O=[N+]([O-])c1cccc(C2CO2)c1 | C(C)(=O)OCC.[BH4-].[Na+].BrCC(=O)C1=CC(=CC=C1)[N+](=O)[O-].[OH-].[K+]>>[N+](=O)([O-])C=1C=C(C=CC1)C1OC1 | Br[CH2:10][C:9]([c:8]1[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:12]1)=[O:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]2[CH2:10][O:11]2)[cH:12]1 | O=C(CBr)c1cccc([N+](=O)[O-])c1 | O=[N+]([O-])c1cccc(C2CO2)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 040b28e8687bbf29652da8799a10f1a268145019b9a625d75da3ba77970763f1 | 98d62a2f88bda9a16db724874a7a21c7201c15ae486e75d3477ada88c887a7ad | c1ccc(C2CO2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[c:5]:[c:4](-[CH;D3;+0:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-1):[c:6] | 110.5 | [{"value": 110.5, "product": "[N+](=O)([O-])C=1C=C(C=CC1)C1OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 10 g of 2-bromo-1-(3-nitro-phenyl)-ethanone is dissolved in 200 ml of ethanol, mixed with 1.55 g of sodium borohydride and stirred for 1 hour at room temperature. 2.1 g of potassium hydroxide is added, and it is stirred for another 15 hours at room temperature. 1000 ml of ethyl acetate is added, and it is washed twice ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ether | null | C1CO1 | c1ccccc1.C1CO1 | Br- | C(C)O | null | 1 | O=C(CBr)c1cccc([N+](=O)[O-])c1>C(C)O>O=[N+]([O-])c1cccc(C2CO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89573fb1735a40b7a8f339fe3cdb01ad | Nc1cccc([N+](=O)[O-])c1.O=C(Cl)OC(=O)Cl>>O=C(CCl)Nc1cccc([N+](=O)[O-])c1 | C([O-])(O)=O.[Na+].C(C)N(CC)CC.ClC(=O)OC(=O)Cl.[N+](=O)([O-])C=1C=C(N)C=CC1>>ClCC(=O)NC1=CC(=CC=C1)[N+](=O)[O-] | [NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14]1.O=[C:3](O[C:2](Cl)=[O:1])[Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | Nc1cccc([N+](=O)[O-])c1.O=C(Cl)OC(=O)Cl | O=C(CCl)Nc1cccc([N+](=O)[O-])c1 | null | null | O1CCCC1 | Acylation | OtherReaction | a9b033e20bc955aa936c36d11128a774c8c1e21a0811bf06c9bccec67a94496f | e5f57d35dff415c079c9c8e252052cdbf0344cead508c414b610a92c42d59fe8 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-[C;H0;D3;+0:3](=O)-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[CH2;D2;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 12 | HOUR | 13.8 g of 3-nitroaniline is dissolved in 500 ml of tetrahydrofuran. 30.5 ml of triethylamine and 19.4 g of chloroformic acid anhydride are added at 0° C. It is stirred for 12 hours at room temperature. The reaction mixture is mixed with semi-saturated sodium bicarbonate solution and extracted with ethyl acetate. The or... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Anhydride.Primary amine | Primary halide.Secondary amide | null | null | c1ccccc1 | Other | O1CCCC1 | null | 12 | Nc1cccc([N+](=O)[O-])c1.O=C(Cl)OC(=O)Cl>O1CCCC1>O=C(CCl)Nc1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b17c81b7874f4b43b33907bc4cd8ca31 | CI.N#CCc1nc2ccccc2[nH]1>>Cn1c(CC#N)nc2ccccc21 | CI.N1C(=NC2=C1C=CC=C2)CC#N.C([O-])([O-])=O.[K+].[K+].O.C([O-])([O-])=O.[K+].[K+].CI>>CN1C(=NC2=C1C=CC=C2)CC#N | I[CH3:1].[nH:2]1[c:3]([CH2:4][C:5]#[N:6])[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][n:2]1[c:3]([CH2:4][C:5]#[N:6])[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | CI.N#CCc1nc2ccccc2[nH]1 | Cn1c(CC#N)nc2ccccc21 | null | null | CO.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b959860a194ba554eb04b7d214c30055f34ef752b392c88b943b67fec007e3e6 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc2[nH]cnc2c1 | I-[CH3;D1;+0:1].[C:2]-[c:3]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[nH;D2;+0:9]:1>>[C:2]-[c:3]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[n;H0;D3;+0:9]:1-[CH3;D1;+0:1] | 14.7 | [{"value": 14.7, "product": "CN1C(=NC2=C1C=CC=C2)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Methyl iodide (1.24 ml, 19.19 mmol) is added to a solution of (1H-benzoimidazol-2-yl)-acetonitrile (3.13 g, 19.91 mmol) and potassium carbonate (2.75 g, 19.91 mmol) in 20 ml of dimethylformamide. It is stirred for 24 hours at room temperature, and additional potassium carbonate (2.8 g, 20.27 mmol) and additional methyl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1 | c1nc2ccccc2[nH]1 | HI | CO.CN(C=O)C | null | 24 | CI.N#CCc1nc2ccccc2[nH]1>CO.CN(C=O)C>Cn1c(CC#N)nc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5714c1ab711a441b8eeeaf43920c65a4 | CCN=C=S.CCOC(=O)CC#N>>CCNC(=S)C(C#N)C(=O)OCC | C(C)N=C=S.C(C)OC(CC#N)=O.C(C)N(CC)CC>>C(C)OC(C(C(NCC)=S)C#N)=O | [CH3:1][CH2:2][N:3]=[C:4]=[S:5].[CH2:6]([C:7]#[N:8])[C:9](=[O:10])[O:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][NH:3][C:4](=[S:5])[CH:6]([C:7]#[N:8])[C:9](=[O:10])[O:11][CH2:12][CH3:13] | CCN=C=S.CCOC(=O)CC#N | CCNC(=S)C(C#N)C(=O)OCC | null | null | O | C-C Coupling | OtherReaction | 323e9a87fd4d443ef5ba4060f0f6f0b4e883d97e756e8c4940c6b61450b6c1c9 | a38abf37d0d52c6966859019a475e360be839ffc5f356447be7c222e97bd82c4 | null | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11]#[N;D1;H0:12]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11]#[N;D1;H0:12])-[C;H0;D3;+0:4](=[S;D1;H0:5])-[NH;D2;+0:3]-[C:2]-[C;D1;H3:1] | null | [] | 50 | CELSIUS | null | null | 4.25 ml of ethyl isothiocyanate is added to a mixture that consists of 5 g of cyanoacetic acid ethyl ester and 5 ml of triethylamine at 25° C. Then, it is allowed to stir for 6 more hours at 50° C. Then, the reaction mixture is concentrated by evaporation in a vacuum. The residue is taken up in ethanol and poured into ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isothiocyanate | Ester.Thioamide | null | null | null | null | O | 50 | null | CCN=C=S.CCOC(=O)CC#N>O>CCNC(=S)C(C#N)C(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51f74bb62445459cbea8a0fe821a842a | C=CCOC(=O)CC#N.CCN=C=S.O=C(Cl)CBr>>C=CCOC(=O)C(C#N)=C1SCC(=O)N1CC | BrCC(=O)Cl.C(C=C)OC(CC#N)=O.[H-].[Na+].C(C)N=C=S.C([O-])(O)=O.[Na+]>>C(C=C)OC(C(=C1SCC(N1CC)=O)C#N)=O | [CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH2:7][C:8]#[N:9].[C:10](=[S:11])=[N:15][CH2:16][CH3:17].Cl[C:13]([CH2:12]Br)=[O:14]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[C:7]([C:8]#[N:9])=[C:10]1[S:11][CH2:12][C:13](=[O:14])[N:15]1[CH2:16][CH3:17] | C=CCOC(=O)CC#N.CCN=C=S.O=C(Cl)CBr | C=CCOC(=O)C(C#N)=C1SCC(=O)N1CC | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 4f26e0c5198f278b78877e80b0522a107fd5230cf75dee13e7680ad9cac269bd | 8f052c6eb6001ef3eeb7218d8ba2c9bed15ebe9ab2aee5d6c2bb042da5af310f | C=C1NC(=O)CS1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3].[C;D1;H2:4]=[C:5]-[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11]#[N;D1;H0:12].[C;D1;H3:13]-[C:14]-[N;H0;D2;+0:15]=[C;H0;D2;+0:16]=[S;H0;D1;+0:17]>>[C;D1;H2:4]=[C:5]-[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:10](-[C:11]#[N;D1;H0:12])=[C;H0;D3;+0:16]1-[S;H0;D2;+... | null | [] | 0 | CELSIUS | null | null | A solution of 37.6 ml of cyanoacetic acid allyl ester in 60 ml of dimethylformamide is added to a suspension of 12.8 g of sodium hydride (60%) in 200 ml of dimethylformamide at 0° C. It is stirred for 10 more minutes at 0° C., and then a solution of 28.0 ml of ethyl isothiocyanate in 60 ml of dimethylformamide is added... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Ester.Isothiocyanate | Enamine.Ester.Tertiary amide.Monosulfide | null | C1CSC[NH]1 | C1CSC[NH]1 | HCl.Br- | CN(C=O)C | 0 | null | C=CCOC(=O)CC#N.CCN=C=S.O=C(Cl)CBr>CN(C=O)C>C=CCOC(=O)C(C#N)=C1SCC(=O)N1CC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-833281a431734f198e35ee414438dcfd | CC(C)(C)OC(=O)N1CCC(=O)CC1.O=C(O)CCc1ccc(F)cc1>>CC(C)(C)OC(=O)N1CCC(O)(C(Cc2ccc(F)cc2)C(=O)O)CC1 | C(CCC)[Li].FC1=CC=C(C=C1)CCC(=O)O.C(C)(C)NC(C)C.C(=O)(OC(C)(C)C)N1CCC(CC1)=O>>C(C)(C)(C)OC(=O)N1CCC(CC1)(O)C(CC1=CC=C(C=C1)F)C(=O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:25][CH2:26]1.[CH2:13]([CH2:14][c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]1)[C:22](=[O:23])[OH:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([OH:12])([CH:13]([CH2:14][c:15]2[cH:16][cH:17][c:1... | CC(C)(C)OC(=O)N1CCC(=O)CC1.O=C(O)CCc1ccc(F)cc1 | CC(C)(C)OC(=O)N1CCC(O)(C(Cc2ccc(F)cc2)C(=O)O)CC1 | null | null | O.C(C)OCC.C1CCOC1 | C-C Coupling | OtherReaction | eeb43c76bf428a561043449a39413034f3f2377495121537b37ca48c390b8557 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(CCC2CCNCC2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[C:5]-[c:6].[O;H0;D1;+0:7]=[C;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-[C:5]-[c:6])-[C;H0;D4;+0:8]1(-[OH;D1;+0:7])-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1 | null | [] | 0 | CELSIUS | 30 | MINUTE | n-Butyllithium (1.6 M in hexane, 8.8 mL, 14.0 mmol) was added dropwise under stirring over 5 min to a cooled solution of N,N-diisopropylamine (2.0 mL, 14.0 mmol) in THF (10 mL) at −40° C. The solution was warmed to 0° C. and a solution of 3-(4-fluoro-phenyl)propionic acid (1.18 g, 7.0 mmol) in THF (8 mL) was added. The... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | null | O.C(C)OCC.C1CCOC1 | 0 | 0.5 | CC(C)(C)OC(=O)N1CCC(=O)CC1.O=C(O)CCc1ccc(F)cc1>O.C(C)OCC.C1CCOC1>CC(C)(C)OC(=O)N1CCC(O)(C(Cc2ccc(F)cc2)C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f532b52311ee49cf9ed40ba685993b7a | C1COCCN1.CC(C)COc1ccc(CN2C(=O)OC3(CCN(C(=O)OC(C)(C)C)CC3)C2Cc2ccc(F)cc2)cc1.ClCCCI>>CC(C)COc1ccc(CN2C(=O)OC3(CCN(CCCN4CCOCC4)CC3)C2Cc2ccc(F)cc2)cc1.Cl.Cl | [I-].[Na+].C(C)(C)(C)OC(=O)N1CCC2(C(N(C(O2)=O)CC2=CC=C(C=C2)OCC(C)C)CC2=CC=C(C=C2)F)CC1.N1CCOCC1.ClCCCI.C([O-])([O-])=O.[K+].[K+]>>Cl.Cl.FC1=CC=C(CC2N(C(OC23CCN(CC3)CCCN3CCOCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1 | [NH:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][C:15]2([O:14][C:12](=[O:13])[N:11]([CH2:10][c:9]3[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([CH3:1])[CH3:3])[cH:40][cH:39]3)[CH:30]2[CH2:31][c:32]2[cH:33][cH:34][c:35]([F:36])[cH:37][cH:38]2)[CH2:29][CH2:28]1.I[CH2:21][CH2:20][CH2:19][Cl:41... | C1COCCN1.CC(C)COc1ccc(CN2C(=O)OC3(CCN(C(=O)OC(C)(C)C)CC3)C2Cc2ccc(F)cc2)cc1.ClCCCI | CC(C)COc1ccc(CN2C(=O)OC3(CCN(CCCN4CCOCC4)CC3)C2Cc2ccc(F)cc2)cc1.Cl.Cl | null | null | C(C)#N.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 5ab09c109745018d60675ce08448c38a0a560a2bef727adf144319f2e2eaf407 | 5c230f77d60fa4c5624050ee0b251756f827227fb0b5e1a6b34dee6818ae30d1 | O=C1OC2(CCN(CCCN3CCOCC3)CC2)C(Cc2ccccc2)N1Cc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].I-[CH2;D2;+0:6]-[C:7]-[CH2;D2;+0:8]-[Cl;H0;D1;+0:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:3]-[C:2]-[N;H0;D3;+0:1](-[CH2;D2;+0:8]-[C:7]-[CH2;D2;+0:6]-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-1)-[C:4]-[C:5].[ClH;D0;+0:9] | 59.6 | [{"value": 40.0, "product": "Cl.Cl.FC1=CC=C(CC2N(C(OC23CCN(CC3)CCCN3CCOCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.6, "product": "Cl.Cl.FC1=CC=C(CC2N(C(OC23CCN(CC3)CCCN3CCOCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | 69NLS77 (300 mg, 0.57 mmol) was N-BOC deprotected as described in the preparation of 69NLS79-II and dissolved in acetonitrile (3 mL) and DMF (1 mL). To a solution of morpholine (65 μL, 0.74 mmol) in acetonitrile (3 mL) and DMF (1 mL) was added dropwise 1-chloro-3-iodopropane (73 μL, 0.68 mmol) and potassium carbonate (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether.Secondary amine.Boc | Tertiary amine.Tertiary amine | C1COCCN1.C1CC2(CC[NH]1)C[NH]CO2 | C1CC2(CC[NH]1)C[NH]CO2.C1COCC[NH]1 | c1ccccc1.C1CC2(CC[NH]1)C[NH]CO2.C1COCC[NH]1.c1ccccc1 | HI | C(C)#N.CN(C)C=O | 50 | 8 | C1COCCN1.CC(C)COc1ccc(CN2C(=O)OC3(CCN(C(=O)OC(C)(C)C)CC3)C2Cc2ccc(F)cc2)cc1.ClCCCI>C(C)#N.CN(C)C=O>CC(C)COc1ccc(CN2C(=O)OC3(CCN(CCCN4CCOCC4)CC3)C2Cc2ccc(F)cc2)cc1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5da7626572c74957b2cdda858e6d26a1 | Fc1ccc(CCBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] | FC1=CC=C(C=C1)CCBr.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].FC1=CC=C(C=C1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][Br:29])[cH:27][cH:28]1.[P:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][P+:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)([c:15]2[cH:16][cH:17... | Fc1ccc(CCBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4].[c:5]:[c:6](-[P;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]):[c:14]>>[Br-;H0;D0:1].[c:5]:[c:6](-[P+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[c:4])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]):[c:14] | null | [] | 200 | CELSIUS | null | null | 4-Fluorophenylethyl bromide (700 mg, 3.44 mmol) was dissolved in toluene (4 mL), triphenylphosphine (904 mg, 3.44 mmol) added and the solution heated for 10 min in a sealed flask at 200° C. under microwave heating. After cooling to rt, the solvent was decanted and the title compound was obtained quantitatively as the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | 200 | null | Fc1ccc(CCBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e77bad5f815f49b48720c15fd9247333 | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.O=C1CCN(C(=O)OCc2ccccc2)CC1>>O=C(OCc1ccccc1)N1CCC(=CCc2ccc(F)cc2)CC1 | [Br-].FC1=CC=C(C=C1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C1CCN(CC1)C(=O)OCC1=CC=CC=C1.O>>C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=CCC1=CC=C(C=C1)F | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)cc1.O=[C:14]1[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:25][CH2:24]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][C:14](=[CH:15][CH... | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.O=C1CCN(C(=O)OCc2ccccc2)CC1 | O=C(OCc1ccccc1)N1CCC(=CCc2ccc(F)cc2)CC1 | null | null | C1CCOC1 | C-C Coupling | Wittig with Phosphonium | ecb4a782aee0dfa853b9f6526be029681ce552b9937de9629d41519dc5ce02fa | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | O=C(OCc1ccccc1)N1CCC(=CCc2ccccc2)CC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]-[C:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:7]-[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 17.2 | [{"value": 17.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=CCC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.2, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=CCC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of phosphonium bromide 78NLS66 (4.69 g, 10.1 mmol) in THF (100 mL) n-butyllithium (1.6 M in hexane, 6.3 mL, 10.1 mmol) was added at 0° C., giving a deep red solution. After stirring for 1 h at rt, a solution of benzyl 4-oxo-1-piperidinecarboxylate (2.24 g, 9.6 mmol) in THF (10 mL) was added dropwise ove... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HO- | C1CCOC1 | null | 1 | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.O=C1CCN(C(=O)OCc2ccccc2)CC1>C1CCOC1>O=C(OCc1ccccc1)N1CCC(=CCc2ccc(F)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-089ed229e2f24d6e980b2a9fdee4f050 | NC(Cc1ccc(F)cc1)C1(O)CCN(C(=O)OCc2ccccc2)CC1>>O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccc(F)cc2)N1 | C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)(O)C(CC1=CC=C(C=C1)F)N.[Na+].[I-].ClCC(=O)Cl.[I-].CC(C)([O-])C>>C(C1=CC=CC=C1)OC(=O)N1CCC2(C(NC(CO2)=O)CC2=CC=C(C=C2)F)CC1 | [OH:4][C:5]1([CH:21]([CH2:22][c:23]2[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]2)[NH2:30])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1>>[O:1]=[C:2]1[CH2:3][O:4][C:5]2([CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18... | NC(Cc1ccc(F)cc1)C1(O)CCN(C(=O)OCc2ccccc2)CC1 | O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccc(F)cc2)N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5aa0679b9babd19a127cd6fe873310338c3a2cb6e7c9839c5c705d57825433d | 3fb4ee9aceabdfb2df4456a679f7c00603ffa8a241c596c92b98a8c6149dbb23 | O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccccc2)N1 | [C:1]-[C:2](-[OH;D1;+0:3])(-[C:4](-[C:5])-[NH2;D1;+0:6])-[C:7]>>[C:1]-[C:2]1(-[C:7])-[O;H0;D2;+0:3]-[C:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:6]-[C:4]-1-[C:5] | 19 | [{"value": 19.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC2(C(NC(CO2)=O)CC2=CC=C(C=C2)F)CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from aminoalcohol 103NLS28 (303 mg, 0.81 mmol) according to literature procedures (Clark et al., J. Med. Chem. 26:855-861 (1983)), by acylation of the amino function with chloroacetylchloride, followed by halogen exchange with NaI and ring closure of the iodide derivative in presence of ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Primary amine | Ether.Secondary amide | null | C1CC2(CC[NH]1)CNCCO2 | C1CC2(CC[NH]1)CNCCO2.c1ccccc1.c1ccccc1 | Other | null | null | null | NC(Cc1ccc(F)cc1)C1(O)CCN(C(=O)OCc2ccccc2)CC1>>O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccc(F)cc2)N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b917275b986452ba34d5f3c89a62702 | CC(C)COc1ccc(CN2C(=O)COC3(CCN(C(=O)OCc4ccccc4)CC3)C2Cc2ccc(F)cc2)cc1>>CC(C)COc1ccc(CN2C(=O)COC3(CCNCC3)C2Cc2ccc(F)cc2)cc1 | C(C1=CC=CC=C1)OC(=O)N1CCC2(C(N(C(CO2)=O)CC2=CC=C(C=C2)OCC(C)C)CC2=CC=C(C=C2)F)CC1>>FC1=CC=C(CC2N(C(COC23CCNCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1 | O=C(OCc1ccccc1)[N:19]1[CH2:18][CH2:17][C:16]2([O:15][CH2:14][C:12](=[O:13])[N:11]([CH2:10][c:9]3[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([CH3:1])[CH3:3])[cH:32][cH:31]3)[CH:22]2[CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:21][CH2:20]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][N:... | CC(C)COc1ccc(CN2C(=O)COC3(CCN(C(=O)OCc4ccccc4)CC3)C2Cc2ccc(F)cc2)cc1 | CC(C)COc1ccc(CN2C(=O)COC3(CCNCC3)C2Cc2ccc(F)cc2)cc1 | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of tertiary amines | af937304b21264b8811b469296e5eb22ab5b770b0214dd2feafbbc70aad61f9b | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C1COC2(CCNCC2)C(Cc2ccccc2)N1Cc1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | null | null | The spirocycle 103NLS33 (62 mg, 0.107 mmol) in ethanol (5 mL) was N-CBz-deprotected by hydrogenation in presence of Pd/C (10%, 40 mg) under H2-balloon pressure. The catalyst was filtered off and the filtrate evaporated under reduced pressure to give crude 5-(4-fluorobenzyl)-4-(4-isobutoxybenzyl)-1-oxa-4,9-diaza-spiro[5... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC2(CC[NH]1)C[NH]CCO2 | C1CC2(CCN1)C[NH]CCO2 | c1ccccc1.C1CC2(CCN1)C[NH]CCO2.c1ccccc1 | HO- | [Pd].C(C)O | null | null | CC(C)COc1ccc(CN2C(=O)COC3(CCN(C(=O)OCc4ccccc4)CC3)C2Cc2ccc(F)cc2)cc1>[Pd].C(C)O>CC(C)COc1ccc(CN2C(=O)COC3(CCNCC3)C2Cc2ccc(F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e73791fe791246daa6f42578abcfb45f | C=C1CC(C(=O)OC)CCN1C(=O)OC(C)(C)C.NN>>CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2 | O.NN.C(=O)(OC(C)(C)C)N1C(CC(CC1)C(=O)OC)=C.C(CCC)O.C(CCC)O>>C(C)(C)(C)OC(=O)N1CCC2(CC(NN2)=O)CC1 | CO[C:15]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:13](=[CH2:14])[CH2:12]1)=[O:16].[NH2:17][NH2:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[CH2:14][C:15](=[O:16])[NH:17][NH:18]2 | C=C1CC(C(=O)OC)CCN1C(=O)OC(C)(C)C.NN | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2 | null | null | null | Acylation | OtherReaction | b8d9c65649ef30778dd60eb750f7c9909f427b3e3792a916b4f4da72c81ba313 | 0b366d061280fe8ca6bc0d693afaacf93e57d2602609b802f5ff0ad42eeec8bd | O=C1CC2(CCNCC2)NN1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C:4]-[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C;H0;D3;+0:14](=[CH2;D1;+0:15])-[C:16]-1.[NH2;D1;+0:17]-[NH2;D1;+0:18]>>[C;D1;H3:11]-[C:10](-[C;D1;H3:12])(-[C;D1;H3:13])-[#8:9]-[C:7](=[O;D1;H0:8])-[#7:6]1-[C:5]-[C:4]-[C;H0... | 63 | [{"value": 63.0, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC(NN2)=O)CC1", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 15 | HOUR | A solution of hydrazine monohydrate (5.28 mL, 108.8 mmol) in n-butanol (20 mL) was added dropwise to a solution of N-BOC-4-methoxycarbonyl-methylenepiperidine (1.39 g, 5.44 mmol) in n-butanol (120 mL) at rt. The mixture was stirred for 15 h at 120° C. and the mixture allowed to cool to rt. The solvent was removed by ev... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Hydrazine.Ester | Acylhydrazine | C1CC[NH]CC1 | C1CC2(CC[NH]1)CCNN2 | C1CC2(CC[NH]1)CCNN2 | HO- | null | 120 | 15 | C=C1CC(C(=O)OC)CCN1C(=O)OC(C)(C)C.NN>>CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c13383252e443d28bfa27d6454508dd | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2.Fc1ccc(CBr)cc1>>CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1 | FC1=CC=C(CBr)C=C1.C(C)(C)(C)OC(=O)N1CCC2(CC(NN2)=O)CC1>>C(C)(C)(C)OC(=O)N1CCC2(CC(NN2CC2=CC=C(C=C2)F)=O)CC1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[CH2:14][C:15](=[O:16])[NH:17][NH:18]2.Br[CH2:19][c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[CH2:14][C:15](=[O:16])[NH:17... | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2.Fc1ccc(CBr)cc1 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | fca470c3b63066e92f5a002ffc705dd1b07dc86a32adac9e07f952920fff7bf5 | 75fa53fcea00b2bf91faff8a86bd2b4c6e278499b46cc76f6552f3496df57ac7 | O=C1CC2(CCNCC2)N(Cc2ccccc2)N1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]1(-[C:7])-[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[NH;D2;+0:12]-1>>[C:5]-[C:6]1(-[C:7])-[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[N;H0;D3;+0:12]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 39 | [{"value": 39.0, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC(NN2CC2=CC=C(C=C2)F)=O)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.0, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC(NN2CC2=CC=C(C=C2)F)=O)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | DAY | 4-Fluorobenzylbromide (0.37 mL, 2.97 mmol) was added dropwise to a solution of 84AF15 (289 mg, 1.13 mmol) in dry DMF (50 mL) at rt. The mixture was stirred at rt for 6 days under argon atmosphere. The solvent was removed by evaporation under reduced pressure and the residue partitioned between chloroform and water. The... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary halide | Acylhydrazine | C1CC2(CC[NH]1)CCNN2 | C1CC2(CC[NH]1)CCN[NH]2 | C1CC2(CC[NH]1)CCN[NH]2.c1ccccc1 | HBr | CN(C)C=O | null | 144 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2.Fc1ccc(CBr)cc1>CN(C)C=O>CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7445d04126a04332b93fac05cbf4a783 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1.CC(C)COc1ccc(CBr)cc1>>CC(C)COc1ccc(CN2C(=O)CC3(CCN(C(=O)OC(C)(C)C)CC3)N2Cc2ccc(F)cc2)cc1 | C(C(C)C)OC1=CC=C(CBr)C=C1.[H-].[Na+].C(C)(C)(C)OC(=O)N1CCC2(CC(NN2CC2=CC=C(C=C2)F)=O)CC1>>C(C)(C)(C)OC(=O)N1CCC2(CC(N(N2CC2=CC=C(C=C2)F)CC2=CC=C(C=C2)OCC(C)C)=O)CC1 | [NH:11]1[C:12](=[O:13])[CH2:14][C:15]2([CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]2)[N:28]1[CH2:29][c:30]1[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]1.Br[CH2:10][c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([CH3:1])[CH3:3])[cH:38][cH:37]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:... | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1.CC(C)COc1ccc(CBr)cc1 | CC(C)COc1ccc(CN2C(=O)CC3(CCN(C(=O)OC(C)(C)C)CC3)N2Cc2ccc(F)cc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1d484d72d1392e1118014cca6a59232f66680d8dcaf2d43a944390da5b781fb8 | 75fa53fcea00b2bf91faff8a86bd2b4c6e278499b46cc76f6552f3496df57ac7 | O=C1CC2(CCNCC2)N(Cc2ccccc2)N1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-1>>[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 50.6 | [{"value": 50.0, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC(N(N2CC2=CC=C(C=C2)F)CC2=CC=C(C=C2)OCC(C)C)=O)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.6, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC(N(N2CC2=CC=C(C=C2)F)CC2=CC=C(C=C2)OCC(C)C)=O)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | NaH (24 mg, 0.50 mmol) was added slowly to a solution of 84AF84-19 (0.149 g, 0.41 mmol) in dry DMF (5 mL) and the mixture stirred at rt for 30 min. A solution of 4-isobutoxybenzyl bromide 69NLS69 (117 mg, 0.48 mmol) in dry DMF (1 mL) was added dropwise to the mixture. After 1 h stirring at rt the mixture was partitione... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary halide | Acylhydrazine | C1CC2(CC[NH]1)CCN[NH]2 | C1CC2(CC[NH]1)CC[NH][NH]2 | c1ccccc1.C1CC2(CC[NH]1)CC[NH][NH]2.c1ccccc1 | HBr | CN(C)C=O | null | 0.5 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1.CC(C)COc1ccc(CBr)cc1>CN(C)C=O>CC(C)COc1ccc(CN2C(=O)CC3(CCN(C(=O)OC(C)(C)C)CC3)N2Cc2ccc(F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98b2c4adc68c4744a60a514a1cbaff45 | CCOc1cccc(N)c1.O=C(O)c1ccccc1I>>CCOc1cccc(Nc2ccccc2C(=O)O)c1 | CCOC1=CC(=CC=C1)N.[OH-].[K+].IC1=C(C(=O)O)C=CC=C1>>C(C)OC=1C=C(C=CC1)NC1=C(C(=O)O)C=CC=C1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[cH:19]1.I[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16](=[O:17])[OH:18]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[OH:18])[cH:19]1 | CCOc1cccc(N)c1.O=C(O)c1ccccc1I | CCOc1cccc(Nc2ccccc2C(=O)O)c1 | null | [Cu] | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | null | [] | null | null | 16 | HOUR | m-Phenetidine (5 ml, 38.7 mmol) is added to a solution of KOH (7.385 g, 131.6 mmol), water (77 ml) and 2-iodobenzoic acid (9.6 g, 38.7 mmol). Powdered copper (77 mg, 1.22 μmol) is added and the mixture is refluxed under stirring over night (16 h).
Conditions: See reaction.notes.procedure_details.
Workup: the mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | [Cu].O | null | 16 | CCOc1cccc(N)c1.O=C(O)c1ccccc1I>[Cu].O>CCOc1cccc(Nc2ccccc2C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86aae17e12b047ba9b4379fbe834604a | COC(=O)C(C)(C)CO.CS>>COC(=O)C(C)(C)CSC | C(C)(C)N(C(C)C)CC.CC(C(=O)OC)(CO)C.[Na].CS.CS(=O)(=O)Cl>>COC(C(CSC)(C)C)=O | O[CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7].[SH:9][CH3:10]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][S:9][CH3:10] | COC(=O)C(C)(C)CO.CS | COC(=O)C(C)(C)CSC | null | null | ClCCl.Cl.C(C)(=O)OCC.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 94a14d3014f7fdb5c4fa6f9f37d523bd85860ea21497647c55ba9393bbc36835 | f8355ba7e68f7d5b10019904f32df628ca7b7bc14adae6579e7d0de9afb40579 | null | O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].[C;D1;H3:9]-[SH;D1;+0:10]>>[C;D1;H3:9]-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8] | 24 | [{"value": 24.0, "product": "COC(C(CSC)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 90 | MINUTE | N,N-Diisopropylethylamine (15.5 g, 0.12 mol) was added to a solution of methyl 2,2-dimethyl-3-hydroxypropionate (13.2 g, 0.1 mol) in dichloromethane (150 mL) and the solution was cooled to 0° C. Methane sulfonyl chloride (12.6 g, 0.11 mol) was then added dropwise and the mixture was stirred at 0° C. for 90 minutes. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aliphatic thiol | Monosulfide | null | null | null | HO- | ClCCl.Cl.C(C)(=O)OCC.O1CCOCC1 | 0 | 1.5 | COC(=O)C(C)(C)CO.CS>ClCCl.Cl.C(C)(=O)OCC.O1CCOCC1>COC(=O)C(C)(C)CSC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c2efaf2eeae4187b51561c68e812e51 | CC#N.CCOC(=O)C(C)(C)SC>>CSC(C)(C)C(=O)CC#N | CC(C(=O)OCC)(C)SC.C(C)#N>>CC(C(CC#N)=O)(C)SC | [CH3:8][C:9]#[N:10].CCO[C:6]([C:3]([S:2][CH3:1])([CH3:4])[CH3:5])=[O:7]>>[CH3:1][S:2][C:3]([CH3:4])([CH3:5])[C:6](=[O:7])[CH2:8][C:9]#[N:10] | CC#N.CCOC(=O)C(C)(C)SC | CSC(C)(C)C(=O)CC#N | null | null | null | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#16:4])(-[C;D1;H3:5])-[C;D1;H3:6].[CH3;D1;+0:7]-[C:8]#[N;D1;H0:9]>>[#16:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9] | 81 | [{"value": 81.0, "product": "CC(C(CC#N)=O)(C)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from ethyl 2-methyl-2-(methylthio)propionate and acetonitrile, using a method similar to that of preparation 2, as a colourless oil in 81% yield.
Conditions: See reaction.notes.procedure_details.
Workup: of preparation 2 | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | null | HO- | null | null | null | CC#N.CCOC(=O)C(C)(C)SC>>CSC(C)(C)C(=O)CC#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a139a84663844002a2a989ff6b313fb6 | CC(C)(C)C(=O)CC#N.CSc1ccc(NN)cc1>>CSc1ccc(-n2nc(C(C)(C)C)cc2N)cc1 | Cl.CSC1=CC=C(C=C1)NN.CC(C(CC#N)=O)(C)C>>C(C)(C)(C)C1=NN(C(=C1)N)C1=CC=C(C=C1)SC | O=[C:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][C:15]#[N:16].[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][NH2:8])[cH:17][cH:18]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[n:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14][c:15]2[NH2:16])[cH:17][cH:18]1 | CC(C)(C)C(=O)CC#N.CSc1ccc(NN)cc1 | CSc1ccc(-n2nc(C(C)(C)C)cc2N)cc1 | null | null | C(C)(=O)OCC.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 5f6cbaa741a86f5065e06033fedb137947fc3a890cbf82b0e291bf675904af0c | a78e9303472e036bbc8878e5b3222e30e9aba072d6de158deb64f510e46fb597 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[NH;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[NH2;D1;+0:4]):[n;H0;D3;+0:10](-[c;H0;D3;+0:1... | 95 | [{"value": 95.0, "product": "C(C)(C)(C)C1=NN(C(=C1)N)C1=CC=C(C=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Concentrated hydrochloric acid (1 mL) was added dropwise to a mixture of 4-methylthiophenyl hydrazine (2 g, 10.5 mmol) and 4,4-dimethyl-3-oxopentane nitrile (1.44 g, 11.5 mmol) in ethanol (30 mL) and the mixture was heated under reflux for 18 hours. The cooled mixture was then diluted with ethyl acetate, washed with sa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile | Primary amine | null | c1cc[nH]n1 | c1ccccc1.c1cc[nH]n1 | HO- | C(C)(=O)OCC.C(C)O | null | null | CC(C)(C)C(=O)CC#N.CSc1ccc(NN)cc1>C(C)(=O)OCC.C(C)O>CSc1ccc(-n2nc(C(C)(C)C)cc2N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-111096eb09634e7ca3c8385e8e5bf841 | CC(C)(C)C(=O)CC#N.NNc1ccccc1>>CC(C)(C)c1cc(N)n(-c2ccccc2)n1 | C(C)(C)N(C(C)C)CC.Cl.C1(=CC=CC=C1)NN.CC(C(CC#N)=O)(C)C>>C(C)(C)(C)C=1C=C(N(N1)C1=CC=CC=C1)N | O=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6][C:7]#[N:8].[NH:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH2:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH2:8])[n:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16]1 | CC(C)(C)C(=O)CC#N.NNc1ccccc1 | CC(C)(C)c1cc(N)n(-c2ccccc2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 5f6cbaa741a86f5065e06033fedb137947fc3a890cbf82b0e291bf675904af0c | a78e9303472e036bbc8878e5b3222e30e9aba072d6de158deb64f510e46fb597 | c1ccc(-n2cccn2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[NH;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[NH2;D1;+0:4]):[n;H0;D3;+0:10](-[c;H0;D3;+0:1... | 70 | [{"value": 70.0, "product": "C(C)(C)(C)C=1C=C(N(N1)C1=CC=CC=C1)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N,N-Diisopropylethylamine (1.7 mL, 7.99 mmol) was added to a mixture of phenyl hydrazine hydrochloride (1.5 g, 10.39 mmol) and 4,4-dimethyl-3-oxopentane nitrile (1.0 g, 7.99 mmol) in ethanol (15 mL) and the mixture was heated under reflux for 18 hours. The cooled mixture was then concentrated to low volume and partitio... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile | Primary amine | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccccc1 | HO- | C(C)O | null | null | CC(C)(C)C(=O)CC#N.NNc1ccccc1>C(C)O>CC(C)(C)c1cc(N)n(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-564c8b5a3bae4c3eadeb4a04bda5ae70 | Clc1ccc(Br)cn1.NN>>NNc1ccc(Br)cn1 | ClC1=NC=C(C=C1)Br.O.NN>>BrC=1C=CC(=NC1)NN | Cl[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][n:9]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][n:9]1 | Clc1ccc(Br)cn1.NN | NNc1ccc(Br)cn1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | bbfd7563459ad1792ea1bdeb15b833ba71625ca5c9310b24f82e4f1a166d7f3e | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 83 | [{"value": 83.0, "product": "BrC=1C=CC(=NC1)NN", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | 2-Chloro-5-bromopyridine (64 g, 333 mmol) was suspended in hydrazine monohydrate (250 mL) and the mixture was heated at 70° C. for 72 hours. The reaction mixture was then diluted with water (750 mL) and the resulting precipitate was filtered off and azeotroped, firstly with toluene (×2) then dichloromethane (×2), to af... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | O | 70 | null | Clc1ccc(Br)cn1.NN>O>NNc1ccc(Br)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7fbae99782c94ec9b01f648e72d53dbe | O=C(O)c1cc(O)ccc1Cl>>OCc1cc(O)ccc1Cl | Cl.ClC1=C(C(=O)O)C=C(C=C1)O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>ClC1=C(C=C(C=C1)O)CO | O=[C:2]([OH:1])[c:3]1[cH:4][c:5]([OH:6])[cH:7][cH:8][c:9]1[Cl:10]>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([OH:6])[cH:7][cH:8][c:9]1[Cl:10] | O=C(O)c1cc(O)ccc1Cl | OCc1cc(O)ccc1Cl | null | null | O1CCCC1.O.O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Lithium aluminium hydride (1M in diethyl ether, 25 mL, 25 mmol) was added to an ice-cooled solution of 2-chloro-5-hydroxy-benzoic acid (4 g, 23.2 mmol) in tetrahydrofuran (200 mL) and the mixture was heated under reflux for 6 hours. The mixture was then diluted with a mixture of water/tetrahydrofuran, acidified with 1M... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1.O.O1CCCC1 | null | null | O=C(O)c1cc(O)ccc1Cl>O1CCCC1.O.O1CCCC1>OCc1cc(O)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00ea2eff8b1942c3a6542fb6da338ae6 | N#Cc1ccc(O)cc1Cl>>O=Cc1ccc(O)cc1Cl | [H-].C(C(C)C)[Al+]CC(C)C.ClC1=C(C#N)C=CC(=C1)O.O1CCCC1.Cl>>ClC1=C(C=O)C=CC(=C1)O | N#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]1[Cl:10]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]1[Cl:10] | N#Cc1ccc(O)cc1Cl | O=Cc1ccc(O)cc1Cl | null | null | O | Functional Group Interconversion | OtherReaction | aa5d6273be01dadb1e5fec75e16ca9b6066d03aa195b40fe3322b26fa6d0b811 | 9f36587406d4620bb1f6625b2c5b8279180c3bebdc2492867ca9e2e72e879d2d | c1ccccc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[O;D1;H0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 84 | [{"value": 84.0, "product": "ClC1=C(C=O)C=CC(=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | Diisobutylaluminium hydride (1M in hexane, 240 mL, 240 mmol) was added to a solution of 2-chloro-4-hydroxybenzonitrile (15 g, 97.7 mmol) in tetrahydrofuran (200 mL), cooled to −78° C., and the mixture was stirred at this temperature for 1 hour then at room temperature for 18 hours. The mixture was then cooled to 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | c1ccccc1 | null | O | -78 | 1 | N#Cc1ccc(O)cc1Cl>O>O=Cc1ccc(O)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b6dba70722745b3994f6a6f7a3b80a5 | CC#N.CCOC(=O)C(C)(C)CC>>CCC(C)(C)C(=O)CC#N | C(C)#N.C(C)OC(C(CC)(C)C)=O.[H-].[Na+]>>CC(C(CC#N)=O)(CC)C | [CH3:8][C:9]#[N:10].CCO[C:6]([C:3]([CH2:2][CH3:1])([CH3:4])[CH3:5])=[O:7]>>[CH3:1][CH2:2][C:3]([CH3:4])([CH3:5])[C:6](=[O:7])[CH2:8][C:9]#[N:10] | CC#N.CCOC(=O)C(C)(C)CC | CCC(C)(C)C(=O)CC#N | null | null | O1CCCC1.Cl | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C;D1;H3:6].[CH3;D1;+0:7]-[C:8]#[N;D1;H0:9]>>[C:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9] | 27 | [{"value": 27.0, "product": "CC(C(CC#N)=O)(CC)C", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | A suspension of sodium hydride (60% dispersion in mineral oil, 3.18 g, 79.4 mmol) in tetrahydrofuran (60 mL) was heated at 60° C. for 1 hour. The reaction mixture was then cooled to room temperature, acetonitrile (4.2 mL, 79.4 mmol) and 2,2-dimethyl-butyric acid ethyl ester [(7.95 g, 61 mmol), J. Am. Chem. Soc., 1942, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | null | HO- | O1CCCC1.Cl | 60 | 4 | CC#N.CCOC(=O)C(C)(C)CC>O1CCCC1.Cl>CCC(C)(C)C(=O)CC#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f091a658fc9f4476afd56d5fa7dad279 | BrCc1ccccc1.Cc1cc(O)cc(Br)c1>>Cc1cc(Br)cc(OCc2ccccc2)c1 | C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+].Cl.BrC=1C=C(C=C(C1)C)O>>C(C1=CC=CC=C1)OC1=CC(=CC(=C1)C)Br | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([OH:8])[cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1 | BrCc1ccccc1.Cc1cc(O)cc(Br)c1 | Cc1cc(Br)cc(OCc2ccccc2)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | null | null | A mixture of 3-bromo-5-methylphenol [(40.7 g, 218 mmol) J. Amer. Chem. Soc., 2003, 125, 7792)], benzyl bromide (28.6 mL, 239 mmol) and potassium carbonate (90.2 g, 653 mmol) in acetone (1 L) was heated under reflux for 2 hours. The cooled reaction mixture was then acidified with 2M hydrochloric acid and the aqueous lay... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | null | BrCc1ccccc1.Cc1cc(O)cc(Br)c1>CC(=O)C>Cc1cc(Br)cc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bc1f55a456e477aad2f6fedd0e10538 | BrCc1ccccc1.N#Cc1ccc(O)cc1Cl>>N#Cc1ccc(OCc2ccccc2)cc1Cl | C([O-])([O-])=O.[K+].[K+].ClC1=C(C#N)C=CC(=C1)O.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC1=CC(=C(C#N)C=C1)Cl | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:15][c:16]1[Cl:17]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]1[Cl:17] | BrCc1ccccc1.N#Cc1ccc(O)cc1Cl | N#Cc1ccc(OCc2ccccc2)cc1Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C#N)C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Potassium carbonate (66.3 g, 480 mmol) was added to a mixture of 2-chloro-4-hydroxybenzonitrile (25 g, 160 mmol) and benzyl bromide (19.3 mL, 161 mmol) in acetonitrile (300 mL) and the mixture was stirred for 18 hours at room temperature. The reaction mixture was then filtered and the filtrate was concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | 18 | BrCc1ccccc1.N#Cc1ccc(O)cc1Cl>C(C)#N>N#Cc1ccc(OCc2ccccc2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9978c40cf11d4fc6912e32bd90f6e968 | CC(=O)c1ccc(Br)cc1O.CI>>CCc1ccc(Br)cc1OC | CI.CC(=O)C1=C(C=C(C=C1)Br)O.C([O-])([O-])=O.[K+].[K+].NN.[OH-].[K+]>>BrC1=CC(=C(C=C1)CC)OC | O=[C:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[OH:10].I[CH3:11]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[O:10][CH3:11] | CC(=O)c1ccc(Br)cc1O.CI | CCc1ccc(Br)cc1OC | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d92841ed14b42889327734c0c9ec1c917040eb4f3d1b5ea3bf8551be02a81c9f | 15778cdfcd04806d9808cb181641e4dda1524030e2da8977ef347ed667b5f6df | c1ccccc1 | I-[CH3;D1;+0:1].O=[C;H0;D3;+0:2](-[C;D1;H3:3])-[c:4](:[c:5]):[c:6](-[OH;D1;+0:7]):[c:8]>>[C;D1;H3:3]-[CH2;D2;+0:2]-[c:4](:[c:5]):[c:6](-[O;H0;D2;+0:7]-[CH3;D1;+0:1]):[c:8] | 1.4 | [{"value": 1.4, "product": "BrC1=CC(=C(C=C1)CC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Methyl iodide (3 mL, 47.3 mmol) was added to a solution of 4-bromo-2-hydroxyacetophenone (9.25 g, 43 mmol) and potassium carbonate (6.54 g, 47.3 mmol) in acetone (20 mL) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo to low volume and diluted with water. The... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic alcohol | Ether | null | null | c1ccccc1 | I- | CC(=O)C | null | 18 | CC(=O)c1ccc(Br)cc1O.CI>CC(=O)C>CCc1ccc(Br)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d836384d371549f6ae742164692af9d8 | COc1cc(N)ccc1Cl>>COc1cc(NN)ccc1Cl | [Sn](Cl)(Cl)(Cl)Cl.N(=O)[O-].[Na+].ClC1=C(C=C(N)C=C1)OC>>ClC1=C(C=C(C=C1)NN)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:8][cH:9][c:10]1[Cl:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][NH2:7])[cH:8][cH:9][c:10]1[Cl:11] | COc1cc(N)ccc1Cl | COc1cc(NN)ccc1Cl | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | 30 | MINUTE | Concentrated hydrochloric acid (12 mL) and a solution of sodium nitrite (1.7 g, 24.4 mmol) in water (8 mL) were added to a solution of 4-chloro-3-methoxy aniline (3.86 g, 24.4 mmol) in water (8 mL), at −10° C. The mixture was stirred for 30 minutes and was then added to solution of tin chloride (14.89 g, 66 mmol) in co... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | 0 | 0.5 | COc1cc(N)ccc1Cl>Cl.O>COc1cc(NN)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4126ddd95368497bb61a6425cfcd157f | CCC(=O)C(C)(C)C.NNc1ccccn1>>CC(C)(C)c1cc(N)n(-c2ccccn2)n1 | N(=O)O.CC(C(CC)=O)(C)C.N(N)C1=NC=CC=C1>>C(C)(C)(C)C1=NN(C(=C1)N)C1=NC=CC=C1 | O=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6][CH3:7].[NH:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1)[NH2:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH2:8])[n:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[n:16]1 | CCC(=O)C(C)(C)C.NNc1ccccn1 | CC(C)(C)c1cc(N)n(-c2ccccn2)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d929e36c72a07fc3af880ff0244c057f94d59a08f33de19ccffd22c475fc1472 | 609b9b28e077105bd6d4464399a572f063ca3c73e05adb7e32c52cfc912dba6d | c1ccc(-n2cccn2)nc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[CH3;D1;+0:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[NH2;D1;+0:8]-[NH;D2;+0:9]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[N;D1;H2:15]):[n;H0;D3;+0:9](-[c;H0;D3;+0:10](:[#7;a:11]:[c... | 99 | [{"value": 99.0, "product": "C(C)(C)(C)C1=NN(C(=C1)N)C1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4,4-dimethyl-3-oxopentane nitrite and 2-hydrazinopyridine, using the same method as that described for preparation 7, as a solid in 99% yield.
Conditions: See reaction.notes.procedure_details.
Workup: that described for preparation 7, as a solid in 99% yield | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Primary amine | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccncc1 | null | null | null | null | CCC(=O)C(C)(C)C.NNc1ccccn1>>CC(C)(C)c1cc(N)n(-c2ccccn2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58885b6c3ef44a14a60079297aafa84d | COC(=O)c1ccc(-n2nc(C(C)(C)C)cc2N)cc1>>CC(C)(C)c1cc(N)n(-c2ccc(CO)cc2)n1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].COC(C1=CC=C(C=C1)N1N=C(C=C1N)C(C)(C)C)=O>>NC1=CC(=NN1C1=CC=C(C=C1)CO)C(C)(C)C | CO[C:14]([c:13]1[cH:12][cH:11][c:10](-[n:9]2[c:7]([NH2:8])[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:18]2)[cH:17][cH:16]1)=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH2:8])[n:9](-[c:10]2[cH:11][cH:12][c:13]([CH2:14][OH:15])[cH:16][cH:17]2)[n:18]1 | COC(=O)c1ccc(-n2nc(C(C)(C)C)cc2N)cc1 | CC(C)(C)c1cc(N)n(-c2ccc(CO)cc2)n1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-n2cccn2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 98 | [{"value": 98.0, "product": "NC1=CC(=NN1C1=CC=C(C=C1)CO)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Lithium aluminium hydride (1M in tetrahydrofuran, 1.83 mL, 1.83 mmol) was added to an ice-cold solution of 4-[5-amino-3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-benzoic acid methyl ester [(0.25 g, 0.92 mmol), WO2004060306, p 134] in tetrahydrofuran (5 mL), and the mixture was stirred at 0° C. for 1 hour. The reaction was t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cc[nH]n1.c1ccccc1 | Other | O1CCCC1 | 0 | 1 | COC(=O)c1ccc(-n2nc(C(C)(C)C)cc2N)cc1>O1CCCC1>CC(C)(C)c1cc(N)n(-c2ccc(CO)cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e4a26af1ad14b9097e73deddfd87a99 | CC(C)(C)[Si](C)(C)Cl.Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1O>>Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1O[Si](C)(C)C(C)(C)C | Cl.NC1=CC(=NN1C=1C=CC(=C(C1)O)C)C(C)(C)C.[Si](C)(C)(C(C)(C)C)Cl>>C(C)(C)(C)C1=NN(C(=C1)N)C1=CC(=C(C=C1)C)O[Si](C)(C)C(C)(C)C | Cl[Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[n:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]2[NH2:15])[cH:16][c:17]1[OH:18]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[n:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]2[NH2:15])[cH:16][c:17]1[O:18][... | CC(C)(C)[Si](C)(C)Cl.Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1O | Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1O[Si](C)(C)C(C)(C)C | null | null | null | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccc(-n2cccn2)cc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 86 | [{"value": 86.0, "product": "C(C)(C)(C)C1=NN(C(=C1)N)C1=CC(=C(C=C1)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 5-[5-amino-3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-methyl-phenol hydrochloride (WO 03/005999, p 81-p 82) and tert-butyldimethylsilyl chloride, using the same method as that described for preparation 99, as a solid in 86% yield.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1.c1cc[nH]n1 | HCl | null | null | null | CC(C)(C)[Si](C)(C)Cl.Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1O>>Cc1ccc(-n2nc(C(C)(C)C)cc2N)cc1O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-476494873d3d4fde90e05deaf6c15c79 | CC(C)(C)C(=O)CC#N.NNc1ccc(OCc2ccccc2)cc1>>CC(C)(C)c1cc(N)n(-c2ccc(OCc3ccccc3)cc2)n1 | CC(C(CC#N)=O)(C)C.Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NN>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)N1N=C(C=C1N)C(C)(C)C | O=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6][C:7]#[N:8].[NH:9]([c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23]1)[NH2:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH2:8])[n:9](-[c:10]2[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH... | CC(C)(C)C(=O)CC#N.NNc1ccc(OCc2ccccc2)cc1 | CC(C)(C)c1cc(N)n(-c2ccc(OCc3ccccc3)cc2)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5f6cbaa741a86f5065e06033fedb137947fc3a890cbf82b0e291bf675904af0c | a78e9303472e036bbc8878e5b3222e30e9aba072d6de158deb64f510e46fb597 | c1ccc(COc2ccc(-n3cccn3)cc2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[NH;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[NH2;D1;+0:4]):[n;H0;D3;+0:10](-[c;H0;D3;+0:1... | null | [] | null | null | null | null | The title compound was prepared from 4,4-dimethyl-3-oxopentane nitrile and 4-benzyloxyphenylhydrazine hydrochloride, using the same method as that described for preparation 7, as a pale pink powder in quantitative yield.
Conditions: See reaction.notes.procedure_details.
Workup: that described for preparation 7, as a pa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile | Primary amine | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)(C)C(=O)CC#N.NNc1ccc(OCc2ccccc2)cc1>>CC(C)(C)c1cc(N)n(-c2ccc(OCc3ccccc3)cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd7d6a053bb9482fa3be474e3c40dc7d | CCCCCN=C=S.N>>CCCCCNC(N)=S | C(CCCC)N=C=S.N>>C(CCCC)NC(=S)N | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]=[C:7]=[S:9].[NH3:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:8])=[S:9] | CCCCCN=C=S.N | CCCCCNC(N)=S | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 9ea44f258f40d07ea72818ac0d167217e6d11d32357aad8e81d4f079b5cbad85 | 8a79caa9356d3b30a3b61a9504f2b151cec34b3b4ac7afcdd36f0060d08e7701 | null | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[NH3;D0;+0:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:6])=[S;D1;H0:5] | 88.4 | [{"value": 88.4, "product": "C(CCCC)NC(=S)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.5, "product": "C(CCCC)NC(=S)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Pentylisothiocyanate (10 g, 0.08 mol) was added slowly (about 10 mins) to a mixture of ammonia (50 mL, 0.2 mol) in methanol (7 N) at 0° C. After being stirred at room temperature for 1 h, the solvent was stripped off and the product was obtained as a white solid (10 g, 88.4%), which was used for next step without furth... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Thiourea | null | null | null | null | CO | null | 1 | CCCCCN=C=S.N>CO>CCCCCNC(N)=S |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6e1d9166c2041abaaf04aa0e2d0a800 | CCCCCNC(N)=S.CCOC(=O)CC#N>>CCCCCn1c(N)cc(=O)[nH]c1=S | C(CCCC)NC(=S)N.C(#N)CC(=O)OCC.[O-]CC.[Na+].C(C)(=O)O>>NC1=CC(NC(N1CCCCC)=S)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:13]([NH2:12])=[S:14].CCO[C:10]([CH2:9][C:7]#[N:8])=[O:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([NH2:8])[cH:9][c:10](=[O:11])[nH:12][c:13]1=[S:14] | CCCCCNC(N)=S.CCOC(=O)CC#N | CCCCCn1c(N)cc(=O)[nH]c1=S | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 7c8d1895dcccf2be52cf37fa9e4ce4c6f1d335657ae7679f46ed9ae391c36484 | 3e8d99e7052416b9a81cbdd8a00ed1d6d130c27ee55193e3ed3c91ce134c8d99 | O=c1cc[nH]c(=S)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;D1;H0:11]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c;H0;D3;+0:9](=[S;D1;H0:11]):[nH;D2;+0:10]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[cH;D2;+0:3]:[c;H0;D3;+0:4]:1-[NH2;D1;+0:5] | 65.5 | [{"value": 65.0, "product": "NC1=CC(NC(N1CCCCC)=S)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.5, "product": "NC1=CC(NC(N1CCCCC)=S)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | N-Pentylthiourea (10.0 g, 0.068 mol) was mixed with ethyl cyanoacetate (9.3 g, 0.082 mol) and sodium ethoxide (6.4 g, 0.094 mol) in ethanol (60 mL). The mixture was stirred at 75° C. overnight. After cooling, a solution of 10% acetic acid in water (150 mL) was added. The solid formed was collected by filtration and was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiourea.Nitrile | Primary amine.Thiocarbonyl | null | c1ccncn1 | c1ccncn1 | HO- | O.C(C)O | 75 | 8 | CCCCCNC(N)=S.CCOC(=O)CC#N>O.C(C)O>CCCCCn1c(N)cc(=O)[nH]c1=S |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-866cc9a3907a4cf9b04e7b8ada8932cc | CCCCCn1c(N)cc(=O)[nH]c1=S>>CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S | NC1=CC(NC(N1CCCCC)=S)=O.N(=O)[O-].[Na+].O>>NC1=C(C(NC(N1CCCCC)=S)=O)N=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([NH2:8])[cH:9][c:12](=[O:13])[nH:14][c:15]1=[S:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([NH2:8])[c:9]([N:10]=[O:11])[c:12](=[O:13])[nH:14][c:15]1=[S:16] | CCCCCn1c(N)cc(=O)[nH]c1=S | CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S | null | null | C(C)(=O)O | Functional Group Addition | OtherReaction | 0552ee48355f6d0f3f2f910735e3f656f8acdaab6c9bb66a1a463b164de8687d | c852dfd7a307035d7b21dc79db1d13bba1cfffe7578c3caa265be3f4f0c038c5 | O=c1cc[nH]c(=S)[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[cH;D2;+0:7]:[c:8]:1-[N;D1;H2:9]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[c;H0;D3;+0:7](-[#7:10]=[O;D1;H0:11]):[c:8]:1-[N;D1;H2:9] | null | [] | 75 | CELSIUS | 1 | HOUR | 6-Amino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (8.0 g, 0.038 mol) was mixed with sodium nitrite (3.1 g, 0.045 mol) in acetic acid (120 mL). The mixture was stirred at 75° C. for 1 h. The color of the reaction mixture became pink and then purple. The solution was allowed to cool down to room temperature, and w... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitroso | c1ccncn1 | c1cncnc1 | c1cncnc1 | Other | C(C)(=O)O | 75 | 1 | CCCCCn1c(N)cc(=O)[nH]c1=S>C(C)(=O)O>CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb554e0db1f346619ab11d7087b5aaed | CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S>>CCCCCn1c(N)c(N)c(=O)[nH]c1=S | S(=O)([O-])S(=O)[O-].[Na+].[Na+].NC1=C(C(NC(N1CCCCC)=S)=O)N=O.N.O>>NC=1C(NC(N(C1N)CCCCC)=S)=O | O=[N:10][c:9]1[c:7]([NH2:8])[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:14](=[S:15])[nH:13][c:11]1=[O:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([NH2:8])[c:9]([NH2:10])[c:11](=[O:12])[nH:13][c:14]1=[S:15] | CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S | CCCCCn1c(N)c(N)c(=O)[nH]c1=S | null | null | C(C)(=O)O | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | O=c1cc[nH]c(=S)[nH]1 | O=[N;H0;D2;+0:1]-[c:2]1:[c:3](=[O;D1;H0:4]):[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:1-[N;D1;H2:10]>>[C:8]-[#7;a:7]1:[c:6]:[#7;a:5]:[c:3](=[O;D1;H0:4]):[c:2](-[NH2;D1;+0:1]):[c:9]:1-[N;D1;H2:10] | 86.1 | [{"value": 86.1, "product": "NC=1C(NC(N(C1N)CCCCC)=S)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.7, "product": "NC=1C(NC(N(C1N)CCCCC)=S)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 5 | MINUTE | To a mixture of 6-amino-1-pentyl-5-nitroso-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (6.4 g, 0.0264 mol), aqueous ammonia (60 mL, 0.60 mol) and water (60 mL) at 75° C. was added sodium dithionite (9.0 g, 0.050 mol) in small portions. After the addition was complete, the color of the solution changed from red to pale yell... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1cncnc1 | Other | C(C)(=O)O | 75 | 0.083333 | CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S>C(C)(=O)O>CCCCCn1c(N)c(N)c(=O)[nH]c1=S |
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