original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
795,050 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][N:12]1[C:20]([C:21]2[N:25]([CH3:26])[CH:24]=[C:23]([C:27]([OH:29])=O)[CH:22]=2)=[C:19]2[C:14]([N:15]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:16](=[O:32])[N:17]([CH3:31])[C:18]2=[O:30])=[N:13]1.Cl.[O:38]([NH2:40])[CH3:39].C(P(=O)(OCC)OCC)#N>>[Cl:1]... | CC(C)Cn1c(=O)n(C)c(=O)c2c(-c3cc(C(=O)O)cn3C)n(Cc3c[nH]c4ccc(Cl)cc34)nc21 | CON | null | CCOP(=O)(C#N)OCC | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was synthesized by the reaction of 5-{2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carboxylic acid and methoxylamine hydrochloride using diethyl cyanophosphonate as a coupling reagent. Mass: 537.98 (M+H). | CONC(=O)c1cc(-c2c3c(=O)n(C)c(=O)n(CC(C)C)c3nn2Cc2c[nH]c3ccc(Cl)cc23)n(C)c1 | null | null | null |
1,338,195 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[N:9][CH:10]=1)=[O:4].[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:7][CH:6]=1)=[O:4].[C:26]([OH:28])([C:25]... | COC(=O)c1cnc(N2CCN(C(=O)OC(C)(C)C)CC2)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 2 | 2-(4-tert-Butoxycarbonyl-piperazin-1-yl)-pyrimidine-5-carboxylic acid methyl ester (140 mg, 0.434 mmol) is dissolved in dichloromethane (3.0 mL) under N2. Trifluoroacetic acid (0.83 ml, 10.85 mmol) is added and the reaction mixture is stirred for 2 h. The reaction mixture is concentrated under reduced pressure and co-e... | COC(=O)c1cnc(N2CCNCC2)nc1 | null | null | null |
1,631,824 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:2]=1.[F:15][C:16]([F:39])([F:38])[CH2:17][CH2:18][C@@H:19](OS(C(F)(F)F)(=O)=O)[C:20]([O:22]CC1C=CC=CC=1)=[O:21]>>[C:11]([O:10][C:8](=[O:9])[C@H:7]([C@@H:19]([CH2:18][CH2:17][C:16]([F:39])([F:38])[F:15])[C:20]([OH:22])=[O:21... | CC(C)(C)OC(=O)Cc1cccnc1 | O=C(OCc1ccccc1)[C@@H](CCC(F)(F)F)OS(=O)(=O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Intermediate S-3 was synthesized from tert-butyl 2-(pyridin-3-yl)acetate (100 mg, 0.517 mmol) and (R)-benzyl 5,5,5-trifluoro-2-(trifluoromethylsulfonyloxy)pentanoate (245 mg, 0.621 mmol) using the procedure described for Intermediate S-2 to give Intermediate S-3 (60 mg, 0.173 mmol) as a white solid containing about 30%... | CC(C)(C)OC(=O)[C@@H](c1cccnc1)[C@@H](CCC(F)(F)F)C(=O)O | null | null | null |
1,073,860 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1 | CC(=O)OC(C)=O | NCCc1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In close analogy to the procedure described above, 2-(4-bromo-phenyl)-ethylamine is reacted with acetic anhydride to provide the title compound. | CC(=O)NCCc1ccc(Br)cc1 | null | null | null |
322,985 | ord_dataset-24ad29d930104afea313b6c3bd11099e | null | 1996-01-01T00:01:00 | true | [C:1]1([CH2:7][N:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH3:26])[N:21]([CH2:22][O:23][CH2:24][CH3:25])[C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:39]1[O:41][CH2:40]1>O1CCCC1>[C:28]1([CH2:27][N:8]([CH2:7][... | C1CO1 | CCOCn1c(C)nc2c(N(Cc3ccccc3)Cc3ccccc3)nc3ccccc3c21 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.08 | A solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.7 g, 3.9 mmole, Example 1 Part E) in tetrahydrofuran (50 mL) was cooled to -78° C. Butyllithium (1.6 mL of 2.5M in hexanes, 4.1 mmole) was added dropwise and the reaction mixture was stirred for 5 minutes. Ethylene oxide wa... | CCOCn1c(CCCO)nc2c(N(Cc3ccccc3)Cc3ccccc3)nc3ccccc3c21 | null | null | null |
650,986 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | [CH3:1][C@H:2]([N:9]=[C:10]=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1>>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:25][CH2:2... | C[C@H](N=C=O)c1ccccc1 | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using an analogous procedure to that described in Example 14, (S)-(−)-α-methylbenzyl isocyanate was reacted with 4-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline to give the title compound; NMR Spectrum: (CDCl3) 1.4-1.56 (m, 2H), 1.61 (d, 3H), 1.84-2.05 (m, 5H), 2.31 (s, 3H), 2.91 (d, 2H), 3.88 (s, 3H), 4... | COc1cc2c(NC(=O)N[C@@H](C)c3ccccc3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null |
293,014 | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | null | 1994-01-01T00:07:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[CH:24][C:18]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][CH:10]=1)#[N:2]>C(O)C>[NH2:28][C:27]1[C:17]([NH:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]... | CCOC(=O)c1cccc([N+](=O)[O-])c1NCc1ccc(-c2ccccc2C#N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | 2 | To a solution of ethyl 2-[(2'cyanobiphenyl-4-yl]-methyl]amino-3-nitrobenzoate (10.4 g) in ethanol (50 ml) was added stannous dichloride dihydrate (28.1 g) and the mixture was stirred at 80° C for two hours. The solvent was evaporated to dryness. To the ice-cooling mixture of the residue in ethyl acetate (300 ml) was ad... | CCOC(=O)c1cccc(N)c1NCc1ccc(-c2ccccc2C#N)cc1 | null | 75.9 | null |
1,297,596 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH3:20])=[C:18](I)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1.C([Mg]Cl)(C)C.CO[B:34]1[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]1.[NH4+].[Cl-]>>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:... | COB1OC(C)(C)C(C)(C)O1 | Cc1c(I)cnn1[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1 | null | CC(C)[Mg]Cl | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-5-methyl-1H-pyrazole (1.15 g, 2.74 mmol) in THF (60 mL, 700 mmol) at rt was added 1.3 M of Isopropylmagnesium Chloride in THF (8.4 mL, 11 mmol), and the mixture was stirred for 1 h. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethy... | Cc1c(B2OC(C)(C)C(C)(C)O2)cnn1[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1 | null | null | null |
1,012,840 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[C:15]([C:20]1([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21]1)[N:14]=2)[C:5](O)=[O:6].[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=... | COCCN | O=C(O)c1ccc(-c2nc3ccc(C4(c5ccccc5)CC4)nc3s2)c(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized using the procedure described in Example 105 above, with 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzoic acid (97 mg, 0.248 mmol) and 2-methoxyethylamine (26 μl, 0.298 mmol). MS (ESI) m/z: Calculated: 447.1; Observed: 448.1 (M++1). | COCCNC(=O)c1ccc(-c2nc3ccc(C4(c5ccccc5)CC4)nc3s2)c(F)c1 | null | null | null |
1,586,873 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:11]([O:21][CH3:22])=[CH:12][CH:13]=[C:14]2[C:19]=1[C:18](=[O:20])[NH:17][CH2:16][CH2:15]2>CN(C)C=O>[NH2:9][C:10]1[C:11]([O:21][CH3:22])=[CH:12][C:13]([Cl:1])=[C:14]2[C:19]=1[C:18](=[O:20])[NH:17][CH2:16][CH2:15]2 | COc1ccc2c(c1N)C(=O)NCC2 | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | N-chlorosuccinimide (20 g, 0.147 mol) was added to a solution of 8-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (296c, 24 g, 0.125 mol) in N,N-dimethylformamide (250 mL) and stirred at room temperature overnight. The solution was partitioned between water (100 mL) and ethyl acetate (5×100 mL). The combined organic ... | COc1cc(Cl)c2c(c1N)C(=O)NCC2 | null | 44.1 | null |
935,883 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)[CH:16]=3)[NH:11][C:10](=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:17]2[C:12](=[CH:13][CH:14... | O=P(Cl)(Cl)Cl | Cc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 | 4 | A mixture of intermediate 22 (0.041 mol) in phosphoryl chloride (105 ml) was stirred at 100° C. for 4 hours then cooled. The solvent was evaporated. The residue was taken up DCM. The solvent was evaporated. The residue was taken up in DCM. The mixture was poured out into ice water, basified with K2CO3 10% and extracted... | Cc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1 | null | 70 | null |
1,599,510 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5](Cl)[S:4][N:3]=1.[CH3:13][CH:14]1[CH2:19][CH2:18][C:17](B(O)O)=[CH:16][CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=C... | CC1CC=C(B(O)O)CC1 | CCOC(=O)c1c(Cl)nsc1Cl | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=P([O-])([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 90 | 8 | Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed ethyl 3,5-dichloro-1,2-thiazole-4-carboxylate (150 mg, 0.66 mmol, 1.00 equiv), (4-methylcyclohex-1-en-1-yl)boronic acid (103 mg, 0.74 mmol, 1.11 equiv), Pd(PPh3)4 (38 mg, 0.03 mmol, 0.05 equiv), K3PO4 (368 mg, 1.73 mmo... | CCOC(=O)c1c(Cl)nsc1C1=CCC(C)CC1 | null | 63.6 | null |
996,111 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [N:1]([C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:22]([CH2:29][CH2:30][CH3:31])[CH2:23][C:24]([O:26]CC)=[O:25].[O-]CC.[Na+:35]>C(O)C.C(OCC)(=O)C>[N:13]1([CH2:12][CH2:11][NH:10][C:8]([C:7]2[CH:6]=[CH:5][C:4]([N:1]3[C:22... | [N-]=[N+]=Nc1ccc(C(=O)NCCN2CCOCC2)cc1 | CCCC(=O)CC(=O)OCC | null | CC[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCO | null | null | null | null | null | null | null | null | null | 25 | 0.33 | 4-Azido-N-(2-morpholin-4-ylethyl)benzamide obtained in Example 61a) and ethyl 3-oxohexanoate (1.07 ml, 6.35 mmol, 1.25 eq.) were dissolved in ethanol (23 ml), sodium ethoxide (480 mg, 6.35 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 20 min, and then at 60° C. for 13 hr. The resulting ... | CCCc1c(C(=O)[O-])nnn1-c1ccc(C(=O)NCCN2CCOCC2)cc1 | null | null | null |
511,138 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [CH2:1]([SH:4])[CH2:2][CH3:3].[H-].[Na+].Cl[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][N:9]=1>C1COCC1>[Cl:14][C:13]1[C:8]([S:4][CH2:1][CH2:2][CH3:3])=[N:9][CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=1 | FC(F)(F)c1cnc(Cl)c(Cl)c1 | CCCS | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 27.5 | 10 | 23.8 g (0.313 mol) of 1-propanethiol were added in the course of 30 minutes to a mixture of 7.9 g (0.313 mol) of 95% pure sodium hydride in 200 ml of THF while flushing with nitrogen and stirring, a temperature of 25-30° C. being maintained by means of cooling. After the mixture had been stirred for 1 hour, 54 g (0.25 ... | CCCSc1ncc(C(F)(F)F)cc1Cl | null | 99.3 | null |
1,187,623 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [CH:1]1([CH:6]=[C:7]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=[C:20... | [H][H] | COc1cnc2[nH]c(C(=CC3CCCC3)c3ccc(S(C)(=O)=O)cc3)cc2c1 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (390 mg, 0.98 mmol) and 10% palladium on activated carbon (50 mg) in methanol (200 mL) was heated at 50° C. under 50 bar of hydrogen in a steel bomb pressure for 6 h. The mixture was cooled to room temperature. The cat... | COc1cnc2[nH]c(C(CC3CCCC3)c3ccc(S(C)(=O)=O)cc3)cc2c1 | null | 61.5 | null |
272,832 | ord_dataset-ee287d49cb8642e59ae9c3951f746312 | null | 1993-01-01T00:08:00 | true | C([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Cl:22])[C:13]=1[NH:23][NH2:24].C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:8][C:7]1[N:23]([C:13]2[C:14]([Cl:22])=[CH:15][C:16]([C:18]([F:19])([F:20])[F:21])=[CH:17][C:12]=2[Cl:11])[N:24]=[C:3]([C:9]#[N... | NNc1c(Cl)cc(C(F)(F)F)cc1Cl | N#CC(C#N)=C(C#N)C#N | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 0.25 | Tetracyanoethylene (1.9 g) and 2,6-dichloro-4-trifluoromethylphenylhydrazine (3.7 g) was added to a magnetically-stirred solution of sodium acetate (0.6 g) in glacial acetic acid (15 ml) at laboratory temperature. After stirring for 15 minutes, a colorless solid precipitated from the solution and stirring was continued... | N#Cc1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(N)c1C#N | null | 48.7 | null |
120,901 | ord_dataset-1d493fcbd5494078b46e816998dcb991 | null | 1984-01-01T00:08:00 | true | [CH3:1][N:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH2:3]1.[N:9]#[C:10][N:11]=[N+]=[N-]>CCOCC>[C:10]([N:11]1[CH:3]2[CH:4]1[C:5]([CH3:8])=[CH:6][CH2:7][N:2]2[CH3:1])#[N:9] | N#CN=[N+]=[N-] | CC1=CCN(C)C=C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1,4-dimethyl-1,2-dihydropyridine (9.69 g, 65 mmol) in ether (10 ml) was added slowly with stirring at 0° C. to a solution of cyanogen azide (5.1 g, 75 mmol). The reaction mixture was allowed to return to 25° C. and the solvent was removed in vacuo to give a reddish-brown product which was partitioned betw... | CC1=CCN(C)C2C1N2C#N | null | 76.2 | null |
335,842 | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | null | 1996-01-01T00:08:00 | true | Br[C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[C:14]=1[CH2:15][O:16][CH3:17])=[CH:11][C:10]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:9][CH:8]=3.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=C... | OB(O)c1ccccc1 | COCc1c(Br)ncc2[nH]c3ccc(OCc4ccccc4)cc3c12 | null | [Pd] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCO | null | null | null | null | null | null | null | null | null | null | 0.08 | 476 mg of 3-bromo-6-benzyloxy-4-methoxymethyl-β-carboline is introduced in 10 ml of toluene and 5 ml of ethanol, mixed with 41 mg of tetrakis(triphenylphosphine)-palladium(0) and stirred for 5 minutes. Then 177 mg of phenylboronic acid and 1.5 ml of a 2 m- soda solution are added and then heated for 3 hours to 95° C. A... | COCc1c(-c2ccccc2)ncc2[nH]c3ccc(OCc4ccccc4)cc3c12 | null | 78.7 | null |
491,183 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15](OCC)=[O:16])[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[NH3:23]>CO>[NH2:23][C:15]([C:13]1[NH:12][C:8]2[N:9]=[CH:10][N:11]=[C:6]([NH:5][C:4]3[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[CH:3]=3)[C:7]=2[CH:14]=1)=[O:16] | CCOC(=O)c1cc2c(Nc3cccc(Cl)c3)ncnc2[nH]1 | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 90 mg (0.285 mmol) of 4-(3-chloroanilino)-6-ethoxycarbonyl-7H-pyrrolo-[2,3-d]pyrimidine (stage 1.4) in 30 ml of methanol and≈5 g of ammonia are heated at 120° C. for 48 h in an autoclave. The reaction mixture is treated with silica gel, evaporated, applied to a silica gel column as a powder and finally eluted with meth... | NC(=O)c1cc2c(Nc3cccc(Cl)c3)ncnc2[nH]1 | null | null | null |
1,200,235 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:15]([O-])=O)[CH:10]=3)[NH:5][C:4]=2[CH2:3]1>CCO.[Pd]>[NH2:15][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]1[CH2:3][N:2]([CH3:1])[CH2:14][CH2:13][C:12]2=1 | CN1CCc2c([nH]c3ccc([N+](=O)[O-])cc23)C1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 20 | To a solution of 2-methyl-6-nitro-2,3,4,9-tetrahydro-1H-β-carboline (description 1) (1.42 g, 6.13 mmol) in EtOH (300 mL), 570 mg of (5%) Pd/C were added. The mixture was hydrogenated under 20 psi at room temperature for 20 h and filtered through a pad of Celite. The EtOH was evaporated to dryness to yield 1.32 g of 6-a... | CN1CCc2c([nH]c3ccc(N)cc23)C1 | null | 107 | null |
735,969 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | Cl.[CH3:2][O:3][C:4](=[O:20])[C@@H:5]([NH2:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[Br:21][C:22]1[CH:23]=[CH:24][C:25]([OH:31])=[C:26]([CH:30]=1)[C:27](O)=[O:28].Cl>CCOC(C)=O>[CH3:2][O:3][C:4](=[O:20])[C@@H:5]([NH:19][C:27](=[O:28])[C:26]1[CH:30]=[C:22]([Br:... | O=C(O)c1cc(Br)ccc1O | COC(=O)[C@@H](N)Cc1ccc(-c2ccccc2)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | 3-Biphenyl-4-yl-(2S)-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester (2.75 g, 35%) was prepared from (2S)-amino-3-biphenyl-4-yl-propionic acid methyl ester-hydrochloride (5.0 g, 17.2 mmol), 5-bromo-2-hydroxy-benzoic acid (3.7 g, 17.2 mmol) as described in general procedure A except for an adapted work-up. ... | COC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1O | null | 35.2 | null |
1,289,978 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18]3[N:26]4[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]4)=[C:20]([C:28]4[CH:29]=[CH:30][C:31]5[C:35]([CH:36]=4)=[N:34][N:33]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:32]=5)[CH:19]=3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)C... | CC(C)(C)OC(=O)N1CCc2ccc(-c3cc(-c4ccc5cn(Cc6ccccc6)nc5c4)c4c(N)ncnn34)cc2C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | To a suspension of 7-[4-amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (2.7 g, 4.7 mmol) in DCM (17 mL) was added TFA (8.6 mL), and the reaction mixture was stirred at rt overnight. The reaction mixture was concentrated and ethyl acet... | Nc1ncnn2c(-c3ccc4c(c3)CNCC4)cc(-c3ccc4cn(Cc5ccccc5)nc4c3)c12 | null | null | null |
1,629,449 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [O:1]([C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C[O-].[Na+].CO>C(OCC)C>[O:23]=[C:17]([CH2:15][C:14](=[O:16])[C:11]1[CH:12]=[N:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][CH:10]=1... | CC(=O)c1cnc(Oc2ccccc2)nc1 | CCOC(=O)C(=O)OCC | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOCC | null | null | null | null | null | null | null | null | null | null | null | A mixture consisting of 1-(2-phenoxypyrimidin-5-yl)ethanone (Example 38, Step B, 214 mg, 1.00 mmol) and diethyl oxalate (0.14 mL, 150 mg, 1.0 mmol) in diethyl ether (10 mL) under a nitrogen atmosphere at room temperature was stirred for ten minutes. Sodium methoxide (65 mg, 1.2 mmol) was subsequently added followed by ... | CCOC(=O)C(=O)CC(=O)c1cnc(Oc2ccccc2)nc1 | null | null | null |
783,246 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [CH3:1][S:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([CH:21]=[C:22]1[S:26][C:25](=[S:27])[NH:24][C:23]1=[O:28])=[CH:10][CH:9]=2)(=[O:4])=[O:3].IC.[CH:31](N(C(C)C)CC)(C)C>C(#N)C>[CH3:1][S:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=... | CS(=O)(=O)c1cnc2ccc(C=C3SC(=S)NC3=O)cc2c1-c1ccccc1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CI | null | null | null | null | null | null | null | null | null | null | null | Similar procedure as described in example 41b was used, starting from 5-(3-methanesulfonyl-4-phenyl-quinolin-6-ylmethylene)-2-thioxo-thiazolidin-4-one (example 61j), iodomethane, and DIEA (diisopropylethylamine) in acetonitrile to give 5-(3-methanesulfonyl-4-phenyl-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one... | CSC1=NC(=O)C(=Cc2ccc3ncc(S(C)(=O)=O)c(-c4ccccc4)c3c2)S1 | null | null | null |
1,725,346 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | C(OC([N:8]1[C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([CH2:27][NH:28][CH2:29][CH3:30])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[O:10]C1(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:12]([CH2:13][F:14])[C@H:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[N:23][C:24]([CH2:2... | CCNCc1ccc(-c2ccc([C@H]3OC(C)(C)N(C(=O)OC(C)(C)C)[C@@H]3CF)cc2)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirred solution of (4S,5R)-5-[4-(6-Ethylaminomethyl -pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.05 g, 0.112 mmol) in CH2Cl2 (0.2 mL) is added trifluoroacetic acid (0.2 mL) at 0° C. Reaction mixture allowed to warm to room temperature and stirred for 2 hours... | CCNCc1ccc(-c2ccc([C@H](O)[C@H](N)CF)cc2)cn1 | null | 117.7 | null |
1,078,102 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])=[C:11]2[O:12][C:13]=1[CH3:14].[H-].[Na+].I[CH2:27][CH2:28][CH3:29]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([N:19]([CH2:27... | CCCI | CCC(=O)Nc1c(C)nn2c(-c3ccc(Cl)cc3Cl)c(C)oc12 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | N-(3-(2,4-Dichlorophenyl)-2,6-dimethylpyrazolo[5,1-b]oxazol-7-yl) propionamide (634 mg, 1.800 mmol) is suspended in dry DMF (20 ml) and treated with NaH (60% in oil) (86 mg, 2.160 mmol) under N2 at RT. The mixture is stirred at RT for 10 minutes before cooling to 0° C. in an ice bath. 1-Iodopropane (0.263 ml, 2.70 mmol... | CCCN(C(=O)CC)c1c(C)nn2c(-c3ccc(Cl)cc3Cl)c(C)oc12 | null | null | null |
868,889 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]([CH:18]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:17])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:31][C:28]1[CH:29]=[CH:30][C:25]([CH:18]([... | BrCc1ccccc1 | CCOC(=O)CC(c1ccc(O)cc1)N(C)C(=O)OC(C)(C)C | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 4 | N,N-Dimethylformamide and benzyl bromide (2.3 ml, 19 mmol) were added sequentially to ethyl 3-[N-(t-butoxy carbonyl)-N-methylamino]-3-(4-hydroxyphenyl)propionate (5.10 g, 16 mmol) obtained from Example 16a and potassium carbonate (3.27 g, 24 mmol) and the mixture was stirred at room temperature for 4 hours. The reactio... | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C | null | 84.2 | null |
1,300,592 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH3:16])[C:13](=[O:15])[CH3:14])=[CH:8][C:6]=2[N:7]=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1B(O)O>>[NH:23]1[C:31]2[C:26](=[C:27]([C:2]3[N:3]=[C:4]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH... | CC(=O)N(C)Cc1cc2nc(Cl)nc(N3CCOCC3)c2s1 | OB(O)c1cc2ccccc2[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | N-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-methyl-acetamide was reacted with indole boronic acid in general procedure A. Purification on silica yielded 193. NMR: 400MHz; CDCl3 2.10, 2.18 (3H,s,2 rotamers); 3.00 (3H,s); 3.84 (4H,m); 4.00 (4H,m); 4.73, 4.77 (2H,s,2 rotamers); 7.26 (2H,m); 7.33 (1H,... | CC(=O)N(C)Cc1cc2nc(-c3cccc4[nH]ccc34)nc(N3CCOCC3)c2s1 | null | null | null |
91,294 | ord_dataset-90c12c4a89ae46d88aea27f4e37ba124 | null | 1982-01-01T00:02:00 | true | [F:1][C:2]([F:13])([F:12])[C:3]1[NH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:7]=1.[Br:14]Br.Cl>C(=O)([O-])[O-].[K+].[K+]>[F:13][C:2]([F:1])([F:12])[C:3]1[NH:4][C:5]([C:8]([F:9])([F:10])[F:11])=[C:6]([Br:14])[N:7]=1 | BrBr | FC(F)(F)c1cnc(C(F)(F)F)[nH]1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2,5-bistrifluoromethylimidazole is dissolved in an aqueous solution of potassium carbonate. Bromine 1.1 equivalents is added and heated until color dissipates. Solution is acidified with dilute hydrochloric acid and extracted with ether. The ether layer is washed once with brine solution, dried over sodium sulfate and ... | FC(F)(F)c1nc(Br)c(C(F)(F)F)[nH]1 | null | 64 | null |
1,327,557 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | CC(S([NH:7][C:8]1([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:11][O:10][CH2:9]1)=O)(C)C.[ClH:18].C(OCC)C>CO>[ClH:18].[N:13]1[CH:14]=[CH:15][CH:16]=[N:17][C:12]=1[C:8]1([NH2:7])[CH2:11][O:10][CH2:9]1 | CC(C)(C)S(=O)NC1(c2ncccn2)COC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CO | null | null | null | null | null | null | null | null | null | 0 | 0.17 | To a yellow solution of 2-methyl-N-(3-(pyrimidin-2-yl)oxetan-3-yl)propane-2-sulfinamide (0.025 g, 0.098 mmol) in MeOH (1 ml) in a 10 ml round-bottomed flask was added a solution of HCl in diethyl ether (0.098 ml, 0.392 mmol, 4N). The reaction mixture was stirred at 0° C. for 10 min., and then concentrated at 25° C. The... | NC1(c2ncccn2)COC1 | null | 93 | null |
1,721,477 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | FC(F)(F)C(O)=O.[N:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[C:14]12[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]1[CH2:17][O:16][NH:15]2>ClCCl>[N:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[C:14]12[CH2:21][NH:20][CH2:19][CH:18]1[CH2:17][O:16][NH:15]2 | CC(C)(C)OC(=O)N1CC2CONC2(c2cnccn2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | Trifluoroacetic acid (40 mL) is added to a stirred solution of tert-butyl 6a-pyrazin-2-yl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (5.14 g, 17.58 mmol) in dichloromethane (200 mL) at room temperature. The mixture is stirred for 1 hour and the solvents are evaporated under reduced pressure. The resul... | c1cnc(C23CNCC2CON3)cn1 | null | 71 | null |
1,655,640 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][C:2]1[N:6]([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH:29]([CH3:33])[NH:28][C:27]=3[CH:26]=[N:25]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH:29]([CH3:... | CC1CCc2c(cnn2-c2ccc(F)cc2)N1 | CCC(C(=O)O)n1nc(C(F)(F)F)cc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoic acid and 1-(4-fluorophenyl)-5-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method A. The reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provid... | CCC(C(=O)N1c2cnn(-c3ccc(F)cc3)c2CCC1C)n1nc(C(F)(F)F)cc1C | null | 46 | null |
1,356,217 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH2:1]([C@@:4]1([CH3:25])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[NH:6][C:5]1=[O:24])[CH:2]=[CH2:3].[H-].[Na+].[N:28]1[CH:33]=[CH:32][C:31](ON2C3C=CC=CC=3N=N2)=[N:30][CH:29]=1>CS(C)=O>[CH2:1]([C@@:4]1([CH3:25])[CH2:9][C@H:8](... | c1ccc2c(c1)nnn2Oc1ccncn1 | C=CC[C@@]1(C)C[C@H](c2cccc(Cl)c2)[C@@H](c2ccc(Cl)cc2)NC1=O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.08 | To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one (Example 71, Step D) (100 mg, 0.27 mmol) in 1.3 mL of DMSO was added sodium hydride (60% suspension in mineral oil, 13 mg, 0.32 mmol) at room temperature. The reaction mixture was stirred for 5 minutes, and was treated wit... | C=CC[C@@]1(C)C[C@H](c2cccc(Cl)c2)[C@@H](c2ccc(Cl)cc2)N(c2ccncn2)C1=O | null | null | null |
783,762 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:33])[C@@H:4]([NH:25]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:22]([C:23]#[N:24])=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[N:18][CH:19]=3)[N:14]=2)=[CH:8][CH:7]=1.[ClH:34]>O1CCOCC1>[ClH:34].[CH3:1][O:2][C:3](=[O:33])[C@@H:4]([NH2:25])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13... | COC(=O)[C@H](Cc1ccc(Nc2nc3ccncc3cc2C#N)cc1)NC(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | (S)-2-tert-Butoxycarbonylamino-3-[4-(3-cyano[1,6]naphthyridin-2-ylamino)phenyl]propionic acid methyl ester (0.12 g) was disolved in dioxane (2 ml) and treated with saturated solution of hydrogen chloride in dioxane (2 ml) for 2 h at room temperature. The solvent was removed under reduced pressure to yield the title com... | COC(=O)[C@@H](N)Cc1ccc(Nc2nc3ccncc3cc2C#N)cc1 | null | 96 | null |
1,449,237 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]1[CH:19]=[C:18]2[C:14]([C:15]3([CH2:24][CH2:23][CH2:22][CH2:21]3)[C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1.Cl.O1CCOC[CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:27])=[O:7])=[CH:4][C:3]=1[C:11]... | Cc1ccc(C(=O)O)cc1-c1ccc2c(c1)NC(=O)C21CCCC1 | C1COCCO1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | null | null | A suspension of 4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzoic acid (preparation 38, 0.47 g, 1.5 mmol) and a 4M solution of hydrochloric acid in dioxane (2.00 mL, 8.0 mmol) in methanol (2 mL) was heated in a sealed tube at 80° C. with stirring. After stirring overnight the mixture was cooled and ethy... | COC(=O)c1ccc(C)c(-c2ccc3c(c2)NC(=O)C32CCCC2)c1 | null | 91.4 | null |
516,913 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | FC(F)(F)S([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])=[CH:11][CH:10]=1)(=O)=O.O[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:20][C:19]([F:22])([F:21])[S:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:... | O=Cc1ccc(O)cc1 | O=S(=O)(OCCc1ccc(OS(=O)(=O)C(F)(F)F)cc1)C(F)(F)F | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 0.85 g (2.11 mmole) of 4-(trifluoromethylsulfonyloxy)phenethyl trifluoromethansulfonate, 0.27 g (2.2 mmole) p-hydroxybenzaldehyde and 0.72 g (2.2 mmole) cesium carbonate in acetonitrile was stirred at room temperature over night. The salts were filtered off and the solvent evaporated in vacuo. Purification... | O=Cc1ccc(OCCc2ccc(OS(=O)(=O)C(F)(F)F)cc2)cc1 | null | 76 | null |
472,789 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | C(=O)([O-])[O-].[Cs+].[Cs+].[CH:7]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]([C:22]3[C:23](=[O:29])[NH:24][C:25](=[O:28])[NH:26][CH:27]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl[CH2:38][C:39]1[N:44]=[C:43]([C:45]([O:47][CH3:48])=[O:46])[CH:42]=[CH:41][CH:40]=1>CS(C)=O>[CH:7]1[C:17... | O=c1[nH]cc(C2c3ccccc3C=Cc3ccccc32)c(=O)[nH]1 | COC(=O)c1cccc(CCl)n1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 4 | Cesium carbonate (1.63 g) was added to a stirred solution of the product of step (iv) (1.5 g) in dimethylsulphoxide (20 ml). After 15 minutes triethylamine (0.71 ml) was added followed by the product from step (ii) (1.11 g). The mixture was stirred at room temperature for 4 hours and partitioned between ethyl acetate a... | COC(=O)c1cccc(Cn2cc(C3c4ccccc4C=Cc4ccccc43)c(=O)[nH]c2=O)n1 | null | null | null |
643,004 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][C:11]([O-:13])=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:14]N(C)CCCN=C=NCC.CCOCC>CC#N.CN(C1C=CN=CC=1)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1 | CCN=C=NCCCN(C)C | O=C([O-])Cc1ccc2c(c1)CCN2 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 18 | Methyl 1-(S-[4-tert-butoxycarbonyl)-4-(tert -butoxycarbonylamino)]butanoyl)indoline-5-acetate 7. Crude 3 (327 mg, 1.9 mmol) was prepared as described above (see compound 4), dissolved in dry MeCN (30 mL) and treated with DMAP (611 mg, 5 mmol) and N-tert-BOC-L-glutamic acid α-tert-butyl ester (607 mg, 2 mmol), followed ... | COC(=O)Cc1ccc2c(c1)CCN2 | null | null | null |
342,022 | ord_dataset-4c84bc8a34e1469aa1b156355c91cdcc | null | 1996-01-01T00:10:00 | true | Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:44]=[CH:43][C:11]([CH:12]=[CH:13][C:14]([NH:16][CH2:17][C:18]([N:20]([C:22]2[C:23]([Cl:42])=[C:24]([C:38]([Cl:41])=[CH:39][CH:40]=2)[CH2:25][O:26][C:27]2[CH:28]=[CH:29][CH:30]=[C:31]3[C:36]=2[N:35]=[C:34]([CH3:37])[CH:33]=[CH:32]3)[CH3:21])=[O:19])=[O:15])=[CH:10][CH:9]=1)=[... | Cc1ccc2cccc(OCc3c(Cl)ccc(N(C)C(=O)CNC(=O)C=Cc4ccc(NC(=O)CCCBr)cc4)c3Cl)c2n1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 16 | To a stirred solution of 8-[3-[N-[4-(bromobutyramido)cinnamoylglycyl]-N-methylamino]-2,6dichlorobenzyloxy]-2-methylquinoline (50 mg) in N,N-dimethylformamide was added potassium carbonate (30 mg) at ambient temperature and the resulting mixture was stirred at the same temperature for 16 hours. The reaction mixture was ... | Cc1ccc2cccc(OCc3c(Cl)ccc(N(C)C(=O)CNC(=O)C=Cc4ccc(N5CCCC5=O)cc4)c3Cl)c2n1 | null | 75.6 | null |
8,409 | ord_dataset-ad879e603f9440f6bfb7fbd18e5e8761 | null | 1976-01-01T00:06:00 | true | [CH3:1][NH:2][O:3][CH3:4].[CH3:5][C:6]1[C:11]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:21][C:22]([OH:24])=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[CH3:4][O:3][N:2]([CH3:1])[C:22](=[O:24])[CH2:21][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([C:12](=[O:20])[C:13]2[CH:14]=[... | CNOC | Cc1c(CC(=O)O)cccc1C(=O)c1ccc(Cl)cc1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | 1 ml of N,O-dimethylhydroxylamine was added progressively to a mixture of 2.88 g of 2-methyl-3-(p-chlorobenzoyl)-phenylacetic acid and 2.06 g. of dicyclohexylcarbodiimide in 50 ml of chloroform and the mixture was stirred for 4 hours at room temperature. The precipitate was filtered off and the filtrate was evaporated ... | CON(C)C(=O)Cc1cccc(C(=O)c2ccc(Cl)cc2)c1C | null | null | null |
167,312 | ord_dataset-fdef1f30cad64430bf05cf108d8004a2 | null | 1988-01-01T00:01:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:18]=2)[N:13]=1>O.C(#N)C>[O:22]([C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]... | Nc1ccc2ccc(Oc3ccccc3)nc2n1 | O=C(O)c1cccc(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | 4 | null | The procedure is analogous to that described in Example 1, but starting with 3-bromobenzoic acid (6 g), N,N'-carbonyldiimidazole (4.9 g) and 2-amino-7-phenoxy-1,8-naphthyridine (5.9 g). The product obtained by precipitation in water (9.8 g; m.p. 188°-192° C.) is dissolved in acetonitrile (300 cc). After cooling for 1 h... | O=C(Nc1ccc2ccc(Oc3ccccc3)nc2n1)c1cccc(Br)c1 | null | 51.7 | null |
955,668 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [C:1]([C:5]1[N:6]=[C:7](Cl)[C:8]2[N:9]([C:11](=[O:14])[NH:12][N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][NH2:26])=[CH:19][CH:18]=1>CN(C=O)C>[C:1]([C:5]1[N:6]=[C:7]([NH:26][CH2:25][CH2:24][O:23][C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)[C:8]... | CC(C)(C)c1cn2c(=O)[nH]nc2c(Cl)n1 | Cc1ccc(OCCN)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | null | To a solution of 60 mg of 6-tert-butyl-8-chloro-2H-[1,2,4]triazolo[4,3-a]pyrazin-3-one and 100 mg of 2-p-tolyloxy-ethylamine hydrochloride in DMF (2.0 mL) was added 60 mg of TEA. The mixture was heated to 80° C. for three h and then was cooled to ambient temperature and partitioned between EtOAc and water. The organic ... | Cc1ccc(OCCNc2nc(C(C)(C)C)cn3c(=O)[nH]nc23)cc1 | null | null | null |
173,294 | ord_dataset-3844acbccc714c04ab757ec4fca10bd0 | null | 1988-01-01T00:06:00 | true | [CH3:1][C:2]1([C:5](=[O:12])[CH2:6][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)[CH2:4][CH2:3]1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(OC(=O)C)(=O)C>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:6]([N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)[C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[O:12])... | CC1(C(=O)Cn2cncn2)CC1 | O=Cc1ccc(Cl)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | 100 | null | 1-(1-Methylcyclopropyl)-2-(1,2,4-triazole-1-yl)ethane-1-one (10 g, 0.06 mole), 4-chlorobenzaldehyde (9 g, 0.06 mole), anhydrous potassium carbonate (8 g, 0.06 mole) and acetic anhydride (100 ml) were mixed, and the mixture was heated to 100° C. for 6 hours with stirring. Precipitates in the reaction solution was remove... | CC1(C(=O)C(=Cc2ccc(Cl)cc2)n2cncn2)CC1 | null | null | null |
1,756,005 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | Br[C:2]1[C:31]2=[N:32][C:28]3=[CH:29][N:30]2[C:5]([N:6]2[CH2:38][CH2:37][C:9]([CH3:39])([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([CH3:36])[O:16][C:17]4[CH:18]=[CH:19][C:20]([F:35])=[C:21]([F:34])[C:22]=4[C:23]4[CH:33]=[C:27]3[CH:26]=[CH:25][CH:24]=4)[CH2:8][CH2:7]2)=[C:4]([C@H:40]([O:45][C:46]([CH3:49])([CH3:48])... | C=Cc1c(C)c([C@H](OC(C)(C)C)C(=O)OC)c2n3cc(nc13)-c1cccc(c1)-c1cc(F)ccc1O[C@@H](C)CCCCOC1(C)CCN2CC1 | COC(=O)[C@@H](OC(C)(C)C)c1c(C)c(Br)c2nc3cn2c1N1CCC(C)(CC1)OCCCC[C@H](C)Oc1ccc(F)c(F)c1-c1cccc-3c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in 52.5% yield from methyl(2S)-2-[(22S)-5-bromo-16,17-difluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]-2-(tert-butoxy)acetate following the procedure for methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-ethenyl-1... | C=Cc1c(C)c([C@H](OC(C)(C)C)C(=O)OC)c2n3cc(nc13)-c1cccc(c1)-c1c(ccc(F)c1F)O[C@@H](C)CCCCOC1(C)CCN2CC1 | null | 52.5 | null |
1,571,231 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:23])[CH:11]=2)[CH:6]=1.[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33].C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][... | Cc1ccccc1S(=O)(=O)Cl | COC(=O)Cc1cc2ccc(Cl)cc2c(-c2ccc(N)cc2)c1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of [4-(4-Amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (100 mg, 0.29 mmol) and 2-Methyl-benzenesulfonyl chloride (113 mg, 0.59 mmol) in THF (5.5 mL) was added diisopropylethylamine (0.15 ml, 0.85 mmol) at 0° C. under nitrogen. After addition, the reaction mixture was warmed to ... | COC(=O)Cc1cc2ccc(Cl)cc2c(-c2ccc(NS(=O)(=O)c3ccccc3C)cc2)c1C | null | 62.8 | null |
1,057,533 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:6](S(C2C=CC=CC=2)(=O)=O)[CH:5]=1)([O-:3])=[O:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18]... | CC(C)(C)OC(=O)Cc1cccc2c1c([N+](=O)[O-])cn2S(=O)(=O)c1ccccc1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a solution of tert-butyl [3-nitro-1-(phenylsulfonyl)-1H-indol-4-yl]acetate from Step C (730 mg, 1.75 mmol) in THF (5 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 5.25 mL, 5.25 mmol) and the reaction mixture was stirred at ambient temperature for 10 min, then concentrated in vacuo. The residue was partiti... | CC(C)(C)OC(=O)Cc1cccc2[nH]cc([N+](=O)[O-])c12 | null | null | null |
1,489,440 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C[Al](C)C.[CH:5]1([CH2:8][NH2:9])[CH2:7][CH2:6]1.C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:23][O:24][C:25]=2[C:26]([F:29])([F:28])[F:27])=[N:15][CH:14]=1.O>O1CCOCC1>[CH:5]1([CH2:8][NH:9][C:12](=[O:11])[C:13]2[CH:18]=[CH:17][C:16]([O:19][... | NCC1CC1 | COC(=O)c1ccc(OCc2c(-c3ccccc3)noc2C(F)(F)F)nc1 | null | C[Al](C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of trimethylaluminium (2 M in toluene, 529 μL, 1.1 mmol) was added dropwise (exothermic) to a solution of cyclopropanemethylamine (75 mg, 91 μL, 1.1 mmol) in dioxane (7 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy... | O=C(NCC1CC1)c1ccc(OCc2c(-c3ccccc3)noc2C(F)(F)F)nc1 | null | 84.8 | null |
876,689 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([C:23]([OH:25])=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1.Cl.[CH3:27][NH:28][O:29][CH3:30]>ClCCl>[CH3:27][N:28]([O:29][CH3:30])[C:23]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1)=[O:25] | O=C(O)c1nccc2ccccc12 | CNOC | null | Cl | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Portions of 1,1′-carbonyldiimidazole (2.06 g, 12.7 mmol) are added to a stirred mixture of isoquinoline-1-carboxylic acid (2.00 g, 11.6 mmol) in dichloromethane (25 ml). N,O-dimethylhydroxylamine hydrochloride (1.24 g, 12.7 mmol) is added and the mixture is stirred at ambient temperature overnight. The reaction mixture... | CON(C)C(=O)c1nccc2ccccc12 | null | 99.7 | null |
694,567 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(=O)[NH:10][CH:9]2[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH... | O=C1NC(Cc2ccc(Oc3ccccc3)cc2)C(c2ccc(F)cc2)O1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of (4RS,5SR)-5-(4-fluorophenyl)-4-((4-(phenyloxy)phenyl)methyl)-1,3-oxazolidin-2-one (2.5 g, 6.88 mmol) in ethanol (20 ml) was added 8N aqueous sodium hydroxide solution (4.30 ml, 34.4 mmol) and the mixture was heated under reflux for 6 hrs. The reaction solution was concentrated, diluted with water (100 ... | NC(Cc1ccc(Oc2ccccc2)cc1)C(O)c1ccc(F)cc1 | null | 94.8 | null |
1,362,205 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | C[O:2][C:3]1[N:8]=[N:7][C:6]([C:9]2[CH:28]=[CH:27][C:12]3[N:13]=[C:14]([N:16]4[CH2:20][CH2:19][C@@H:18]([N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]5)[CH2:17]4)[S:15][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.Br>>[N:21]1([C@@H:18]2[CH2:19][CH2:20][N:16]([C:14]3[S:15][C:11]4[CH:10]=[C:9]([C:6]5[N:7]=[N:8][C:3]([OH:2])=[CH:4][... | COc1ccc(-c2ccc3nc(N4CC[C@@H](N5CCCCC5)C4)sc3c2)nn1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of (R)-6-(6-methoxypyridazin-3-yl)-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole (Example 68, 19.8 mg, 0.032 mmol) in hydrobromic acid (48 wt. % in water, 0.25 mL, 2.210 mmol) was heated to 80° C. for 1 hour, concentrated with a stream of nitrogen and chromatographed on silica gel eluting with a grad... | Oc1ccc(-c2ccc3nc(N4CC[C@@H](N5CCCCC5)C4)sc3c2)nn1 | null | null | null |
884,956 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [CH2:1]([O:3][C:4](=[O:7])[C:5]#[N:6])[CH3:2].[CH2:8]([OH:10])[CH3:9]>C(OCC)C>[CH2:1]([O:3][C:4](=[O:7])[C:5]([O:10][CH2:8][CH3:9])=[NH:6])[CH3:2] | CCOC(=O)C#N | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 40 | null | Nitriloacetic acid ethyl ester (83 mmol) was dissolved in diethyl ether (water free, 25 ml) and ethanol (water free, 85 mmol) was added and the stirred mixture cooled to 40 ° C. At this temperature, HCl (gaz, dried through concentrated sulfuric acid; 18 g total consumption) was bubbled into the solution over 1 hour. Th... | CCOC(=N)C(=O)OCC | null | null | null |
1,182,107 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C@@H:12](O)([CH2:14][CH3:15])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:13][C@@H:12]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH2:14][CH3:15] | COC(=O)c1cccc(O)c1 | CC[C@H](C)O | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | To a 0° C. solution of methyl 3-hydroxybenzoate (5.00 g, 32.9 mmol) in toluene (32.9 ml) was added (S)-(+)-sec-butanol (3.34 ml, 36.1 mmol), triphenylphosphine (9.48 g, 36.1 mmol), and DIAD (7.03 ml, 36.1 mmol). After warming to rt overnight, the reaction mixture was filtered through a fritted funnel and washed with to... | CC[C@@H](C)Oc1cccc(C(=O)OC)c1 | null | null | null |
648,296 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[CH3:11][C:12]1[C:18]([CH3:19])=[CH:17][C:15]([NH2:16])=[C:14]([N+:20]([O-:22])=[O:21])[CH:13]=1>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:16][C:15]2[CH:17]=[C:18]([CH3:19])[C:12]([CH3:11])=[CH:13][C:14]=2[N+:20]([O-:22])=[O:21])=[O:7])=[CH:9][CH:10]=1 | O=C(Cl)c1ccc(Cl)nc1 | Cc1cc(N)c([N+](=O)[O-])cc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 6-chloronicotinoyl chloride and 4,5-dimethyl-2-nitroaniline and was obtained as an orange solid as described in Example 1. 1H NMR (CDCl3): 11.38 (s, 1H), 9.03 (d, J=2.1, 1H), 8.72 (s, 1H), 8.24-8.21 (m, 1H), 8.07 (s, 1H), 7.52 (d, J=8.7, 1H), 2.41 (s, 3H), 2.34 (s, 3H). | Cc1cc(NC(=O)c2ccc(Cl)nc2)c([N+](=O)[O-])cc1C | null | null | null |
588,215 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [CH:1]1([NH:7][C:8]([NH2:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O>>[CH2:4]1[CH2:5][CH2:6][CH:1]([N:7]=[C:8]=[N:10][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:2][CH2:3]1 | NC(=O)NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 5 | The polymer bound cyclohexylurea (PS-DCU; 1 g of 1.25 mmol/g) recovered after N-acylation is suspended in dichloromethane (20 ml) in a two-necked round-bottom flask (100 ml) equipped with a silicone rubber septum and a reverse filter funnel under exclusion of moisture and air. Phosphorus oxychloride (POCl3; 0.38 g, 2.5... | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null |
887,653 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:15]2[O:14][N:13]=[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]#[N:26])[CH2:18][CH2:17]3)[C:11]=2[S:10][CH:9]=1>O1CCCC1>[CH3:7][C:8]1[C:15]2[O:14][N:13]=[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:18][CH2:17]3... | Cc1csc2c(C3CCN(CCCC#N)CC3)noc12 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2.5 | Under inert conditions, add lithium aluminum hydride (3.42 mmol, 3.42 mL, 1.50 equivalents, 1.0 M solution in tetrahydrofuran) to a stirred solution of 4-[4-(6-methyl-thieno[2,3-d]isoxazol-3-yl)-piperidin-1-yl]-butyronitrile (2.28 mmol, 660 mg, 1.00 equivalents) in tetrahydrofuran (dry, 12.86 mL). Stir the resulting so... | Cc1csc2c(C3CCN(CCCCN)CC3)noc12 | null | 68.3 | null |
1,230,794 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [CH:1]1([N:7]2[C:12]([OH:13])=[C:11]([C:14]([NH:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:15])[C:10](=[O:23])[NH:9][C:8]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH:31]1([CH2:37][CH2:38]Br)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.Cl>CC(N(C)C)=O>[CH:1]1([N:7]2[C:12]([OH:13])=[C:11]([C:14]([N... | BrCCC1CCCCC1 | CCOC(=O)CNC(=O)c1c(O)n(C2CCCCC2)c(=O)[nH]c1=O | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | null | 8 | A mixture of ethyl N-[(1-cyclohexyl-6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycinate (340 mg, 1.0 mmoles), pulv. potassium carbonate (1.0 g, 7.24 mmoles) and 2-cyclohexylethyl bromide (287 mg, 1.5 mmoles) in dimethylacetamide (8 mL) was vigorously stirred at 100° C. for 3 hours. The mixture was p... | O=C(O)CNC(=O)c1c(O)n(C2CCCCC2)c(=O)n(CCC2CCCCC2)c1=O | null | 42.7 | null |
865,008 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][N:26]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:1... | CC(C)(C)OC(=O)COCCOCCOCCOCCOCCOCCN=[N+]=[N-] | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCO | null | null | null | null | null | null | null | null | null | null | 16 | To a solution of compound 4 (1.0 g, 2.4 mmol) in ethanol (20 mL) was added 10% Pd/C (0.3 g) and acetic acid (0.3 mL). The resulting mixture was stirred under an atmosphere of hydrogen for 16 hours and then filtered to remove Pd/C. The filtrate was concentrated in vacuo and the residue was loaded onto a silica gel gravi... | CC(C)(C)OC(=O)COCCOCCOCCOCCOCCOCCN | null | 94.8 | null |
1,646,046 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:17]3[CH:16]=[C:15]4[CH2:18][CH2:19][CH2:20][C:21](=[O:22])[C:14]4=[CH:13][C:12]=3[O:11][CH2:10][C:9]=2[CH:23]=1)=[O:4].[C:24]([O:28][C:29]([N:31]1[CH2:35][C@@H:34]([CH2:36][O:37][CH3:38])[CH2:33][C@H:32]1[C:39]([OH:41])=[O:40])=[O:30])([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])... | O=C(CBr)c1ccc2c(c1)COc1cc3c(cc1-2)CCCC3=O | COC[C@H]1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 4 | 3-(2-Bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (7.47 g, 20.1 mmol) and (2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid (5.22 g, 20.1 mmol) were suspended in 2-Me-THF (75 mL) and treated with Cs2CO3 (3.27 g, 10.1 mmol). After stirring 4 h at RT, the reaction mixture was d... | COC[C@H]1CC(C(=O)OCC(=O)c2ccc3c(c2)COc2cc4c(cc2-3)CCCC4=O)N(C(=O)OC(C)(C)C)C1 | null | 70 | null |
800,789 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | [O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C[O:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>CCOCC>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:18][CH:19]=1 | COc1ccc(C=CC(=O)O)cc1 | C1=COCCC1 | null | Cc1ccc(S(=O)(=O)O)cc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 0 | 1 | 14 ml of dihydropyran was added dropwise to a mixture of 17.8 g of 4-methoxycinnamic acid, 0.34 g of 4-toluene sulphonic acid and 100 ml of diethyl ether under a nitrogen atmosphere. After one hour stirring the solution became transparent. 150 ml of ether was added and it was extracted with 200 ml of 5% of sodium hydro... | O=C(O)C=Cc1ccc(OC2CCCCO2)cc1 | null | 79 | null |
1,359,796 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](O)=[O:12])[CH:6]=[CH:7][CH:8]=1.CSC.B.Cl>O1CCCC1>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1 | O=C(O)CCc1cccc(C(F)(F)F)c1 | null | null | B | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CSC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 2.5 | null | Compound obtained from Example 1 (0.463 moles, 100 gms) was suspended in 500 ml of tetrahydrofuran under stirring. The reaction mass was cooled to 0-5° C. 94% solution of borane dimethyl sulfide solution (0.62 moles, 50 ml) was added drop wise maintaining the temperature of 0-5° C. The reaction mass was stirred at 25-3... | OCCCc1cccc(C(F)(F)F)c1 | null | 89.9 | null |
222,928 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | [CH2:1]([N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>C1C=CC=CC=1>[CH2:1]([N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[S:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][... | S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CCCCCCCCCCCCN1CCCCCC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 5g (17.7mmol) of 1-n-dodecylazacycloheptan-2-one in 150ml of benzene was added 4.18g (9.4mmol) of phosphorus pentasulfide and the mixture was refluxed for 1 hr. After cooling to room temperature, the mixture was filtered and the solid was washed with chloroform and ethanol. The filtrate was concentrate... | CCCCCCCCCCCCN1CCCCCC1=S | null | 40 | null |
1,613,518 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | Br[CH:2]([C:6]1[S:7][C:8]([C:17]2[N:21]=[CH:20][N:19](C3CCCCO3)[N:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)[C:3]([CH3:5])=O.[NH2:28][C:29]1[S:30][CH:31]=[C:32]([CH3:34])[N:33]=1.Cl.[OH-].[Na+]>C1COCC1.CC(O)C>[CH3:34][C:32]1[N:33]2[C:2]([C:6]3[S:7][C:8]([C:17]4[N:21]=[CH:20][NH:19][N:18]=4)=[... | CC(=O)C(Br)c1nc(-c2ccccc2)c(-c2ncn(C3CCCCO3)n2)s1 | Cc1csc(N)n1 | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 80 | 4 | To a mixture of 1-bromo-1-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}acetone (1.15 g, 2.5 mmol) obtained by similar manner with Example 116-B(vi) in THF (12.5 mL) and 2-propanol (12.5 mL), was added 2-amino-4-methylthiazole (1.43 g, 12.5 mmol), the mixture was stirred at 80° C. fo... | Cc1nc2scc(C)n2c1-c1nc(-c2ccccc2)c(-c2nc[nH]n2)s1 | null | 9.3 | null |
1,690,972 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11](COCC[Si](C)(C)C)[N:10]=2)=[N:6][C:7]=1F.Cl.[NH:33]1[CH2:38][CH2:37][CH2:36][C@@H:35]([OH:39])[CH2:34]1>>[Br:1][C:2]1[C:7]([N:33]2[CH2:38][CH2:37][CH2:36][C@@H:35]([OH:39])[CH2:34]2)=[N... | O[C@@H]1CCCNC1 | C[Si](C)(C)CCOCn1nc(-c2ccc(Br)c(F)n2)c2cc(-c3cccnc3)ncc21 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedures as described in Example 241 and starting with 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and (R)-piperidin-3-ol hydrochloride, 291 was obtained as an off-white solid (11.0 mg, 29.9%) over two steps. 1H NMR (400 MHz, DMSO) δ ... | O[C@@H]1CCCN(c2nc(-c3n[nH]c4cnc(-c5cccnc5)cc34)ccc2Br)C1 | null | 29.9 | null |
1,570,666 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:30])[CH:25]=[CH:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:2... | C1COCCN1 | CCCC=CC(=O)N1CCC(N(C2CC2)S(=O)(=O)c2cccc(C(F)(F)F)c2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | N-Cyclopropyl-N-[1-(3-morpholin-4-yl-hexanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (42) was prepared by reacting N-cyclopropyl-N-(1-hex-2-enoyl-piperidin-4-yl)-3-trifluoromethylbenzene-sulfonamide (30) (250 mg, 0.56 mmol) and morpholine (2 mL) as described in Example 26 above. The residue was chromatogra... | CCCC(CC(=O)N1CCC(N(C2CC2)S(=O)(=O)c2cccc(C(F)(F)F)c2)CC1)N1CCOCC1 | null | 40 | null |
453,633 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:27]1([CH2:33][S:34][CH:35]([C:39](O)=[O:40])[C:36](O)=[O:37])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:11][C:36](=[O:37])[C:35]([S:34][CH2:33][C:27]3[... | O=C(O)C(SCc1ccccc1)C(=O)O | CC(=O)c1cc(C)cc(C)c1 | null | C[Si](C)(C)Cl | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by Method A using 3',5'-dimethylacetophenone (0.785 g, 5.31 mmol), lithium bis(trimethylsilyl)amide (0.977 g, 5.84 mmol), chlorotrimethylsilane (0.741 mL, 5.84 mmol), THF (58 mL), and diethyl ester of [(phenylmethyl)thio]propanedioic acid (1.00 g, 3.54 mmol). m.p. dec. 170° C.; 1H NMR (4... | Cc1cc(C)cc(-c2cc(O)c(SCc3ccccc3)c(=O)o2)c1 | null | null | null |
209,707 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | C(OC([O:6][CH2:7][C:8]#[C:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11])C)C.Cl>O1CCCC1>[OH:6][CH2:7][C:8]#[C:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)=[O:11] | CCOC(C)OCC#CC(=O)c1ccc(OC)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.5 | A solution of 7.3 g (27.8 mmol) of 4-(1-ethoxyethoxy)-1-(4-methoxyphenyl)-2-butyn-1-one in 95 ml of tetrahydrofuran was treated at room temperature with 28 ml of 2N hydrochloric acid, whereupon the mixture was stirred for 30 minutes. The reaction mixture was then extracted twice with ethyl acetate. The combined organic... | COc1ccc(C(=O)C#CCO)cc1 | null | null | null |
193,070 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23](O)=[O:24])[NH:8][CH2:7][CH2:6]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:14][O:13][C:12]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:23](=[O:24])[CH2:22]... | COc1cc2c(cc1OC)C(Cc1ccccc1CC(=O)O)NCC2 | null | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 6 | To an ice-chilled solution of 2-[(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolinyl)methyl]benzeneacetic acid (XIc, Ex. 16) (0.4 g, 1.17 mmole) and 4-dimethylaminopyridine (0.15 g, 1.23 mmol) in dry acetonitrile (45 ml) was added with stirring dicyclohexylcarbodiimide (0.24 g, 1.17 mmole). The resulting mixture was stirred... | COc1cc2c(cc1OC)C1Cc3ccccc3CC(=O)N1CC2 | null | 68.7 | null |
1,580,624 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15]C)=[O:14])[C:7](=[O:17])[CH2:6]2>O1CCOCC1.Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7](=[O:17])[CH2:6]2 | COC(=O)CN1C(=O)Cc2cc(OC)ccc21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of methyl 2-(5-methoxy-2-oxoindolin-1-yl)acetate (350 mg, 1.488 mmol) in dioxane (10 ml), 12N HCl (10 ml) was added, and the mixture was stirred at room temperature for 24 hours. Then the solvent was evaporated and the resulting crude was dissolved in MeOH (5 ml); by addition of iPrO2 (50 ml) the title co... | COc1ccc2c(c1)CC(=O)N2CC(=O)O | null | 61 | null |
1,215,522 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]([CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17]#[N:18])[C:12](=[O:23])[N:11]([CH2:24]C3C=CC=C(C#N)C=3)[C:10](=[O:33])[CH:9]=2)[CH2:3]1.BrC[C:36]1[C:37]([C:42]#[N:43])=[CH:38][CH:39]=[CH:40][CH:41]=1>>[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:... | N#Cc1ccccc1CBr | N#Cc1cccc(Cn2c(=O)cc(N3CCC[C@@H](N)C3)n(Cc3ccccc3C#N)c2=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Title compound 18 was prepared by the methods used in the preparation of compound 17, except that α-bromo-o-tolunitrile was used in the place of m-cyano-benzyl bromide. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1) δ 7.64 (d, J=6.8 Hz, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.55 (t, J=7.8 Hz, 2 H), 7.44 (t, J=7.6 Hz, 1 H), 7.38 (t, J=7.5 H... | N#Cc1ccccc1Cn1c(N2CCC[C@@H](N)C2)cc(=O)n(Cc2ccccc2C#N)c1=O | null | null | null |
705,788 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:12]=1[O:23][CH3:24].[I-:25].[Na+]>CC(C)=O>[I:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21]... | COC(=O)/C=C/c1ccc(OCCCCCCCCCl)c(OC)c1 | [I-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | 26.8 g (75.52 mmol) methyl (2E)-3-{4-[(8-chloroctyl)oxy]-3-methoxyphenyl}-2-propenoate was dissolved in 1000 ml acetone. 65.16 g (435.15 mmol) sodium iodide were added. The reaction suspension was heated at reflux temperature for 24 hours. The reaction mixture was partitioned between diethylether and water. The organic... | COC(=O)/C=C/c1ccc(OCCCCCCCCI)c(OC)c1 | null | 89.3 | null |
1,456,671 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [N:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:6][CH:5]=1)=[C:2]=[O:3].Cl.[NH2:20][CH2:21][C:22]([NH2:24])=[O:23].C(N(CC)CC)C>C1COCC1>[CH3:17][C:12]1([CH3:18])[C:13]([CH3:16])([CH3:15])[O:14][B:10]([C:7]2[CH:8]=[CH:9][C:4]([NH:1][C:2](=[O:3])[NH:20][CH2:21][... | NCC(N)=O | CC1(C)OB(c2ccc(N=C=O)cc2)OC1(C)C | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 2-(4-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 mg, 1.22 mmol) was dissolved in dry THF and stirred with 2-aminoacetamide hydrochloride (108 mg, 1.46 mmol) and triethylamine (drops) at 60° C. overnight. The mixture was reduced in vacuo, yielding the title compound (345 mg, 1.08 mmol, 88%). | CC1(C)OB(c2ccc(NC(=O)NCC(N)=O)cc2)OC1(C)C | null | 88.5 | null |
1,659,663 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([CH2:38]Br)[CH:29]=1>C(#N)C>[Br:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:3... | COC(=O)c1ccc(Br)cc1CBr | O=c1[nH]nc(-c2ccc(Cl)cc2)n1CC(O)C(F)(F)F | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | 450 mg (1.30 mmol) of the compound from Example 4A and 715 mg (2.19 mmol) of cesium carbonate were suspended in 6 ml of acetonitrile, and 708 mg (1.61 mmol) of methyl 4-bromo-2-(bromomethyl)benzoate were added. The mixture was stirred under reflux for 20 h. The precipitated solid was filtered off and the filtrate was c... | COC(=O)c1ccc(Br)cc1Cn1nc(-c2ccc(Cl)cc2)n(CC(O)C(F)(F)F)c1=O | null | null | null |
91,796 | ord_dataset-90c12c4a89ae46d88aea27f4e37ba124 | null | 1982-01-01T00:02:00 | true | [C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]([Cl:22])([Cl:21])[CH:7]([OH:20])[CH:8]([N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)[C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]>CN(C)C=O>[Cl:22][C:6]([Cl:5])([Cl:21])[CH:7]([O:20][C:1](=[O:3])[CH3:2])[CH:8]([N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)[C:9](=[O:14])[C:10]([CH3:12])([CH3:13])[C... | CC(C)(C)C(=O)C(C(O)C(Cl)(Cl)Cl)n1cncn1 | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 8.0 g (0.1 mol) of acetyl chloride were added to 31.5 g (0.1 mol) of 1,1,1-trichloro-2-hydroxy-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-hexan-4-one in 100 ml of dimethylformamide at room temperature. Thereafter, the mixture was heated under reflux for 4 hours. It was left to cool and concentrated by distilling off the solve... | CC(=O)OC(C(C(=O)C(C)(C)C)n1cncn1)C(Cl)(Cl)Cl | null | 40.1 | null |
1,049,691 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]3[N:19]=[CH:20][N:21]([CH3:22])[C:13]=3[CH:12]=2)=[CH:7][C:6]=1[C:23]([F:26])([F:25])[F:24].[O:27]=[C:28]1[CH2:33][NH:32][CH2:31][CH2:30][NH:29]1>CN(C=O)C>[CH3:22][N:21]1[C:13]2[CH:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][CH2:... | O=C1CNCCN1 | Cn1cnc2c(C#N)nc(-c3ccc(CCCBr)c(C(F)(F)F)c3)cc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 6-(4-(3-Bromopropyl)-3-(trifluoromethyl)-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (50 mg) and 2-oxopiperazine (103 mg) in DMF (750 μl) were heated at 100° C. in a microwave for 25 minutes. Purification by basic phase preparative LCMS afforded 1-methyl-6-{4-[3-(3-oxo-piperazin-1-yl)-propyl]-3-trifluorom... | Cn1cnc2c(C#N)nc(-c3ccc(CCCN4CCNC(=O)C4)c(C(F)(F)F)c3)cc21 | null | 28.7 | null |
383,028 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.C(N(CC)CC)C>C(O)C>[N+:18]([C:17]1[C:12]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[N:13][CH:14]=[CH:15][CH:16]=1)([O-:20])=[O:19] | Nc1ccc2[nH]ccc2c1 | O=[N+]([O-])c1cccnc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | null | 5-Aminoindole (0.264 g, 2.00 mmoles) and 2-chloro-3-nitropyridine (0.476 g, 3.00 mmoles) were combined with triethylamine (0.42 ml, 3.01 mmoles) in absolute ethanol. The reaction was heated at room temperature under nitrogen for 72 hours. The resulting reaction mixture was filtered to afford the title compound (69%) as... | O=[N+]([O-])c1cccnc1Nc1ccc2[nH]ccc2c1 | null | 69 | null |
1,466,986 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:14]1[N:15]([CH2:27][C:28]#[CH:29])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1)[CH3:13]>C(Cl)(Cl)Cl>[CH2:12]([C:14]1[N:15]([CH2:27][C:28]#[CH:29])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:19]([O-:6])=[CH:18][C:17]=2[N:26]=1)[CH3:... | O=C(OO)c1cccc(Cl)c1 | C#CCn1c(CC)nc2cnc3ccccc3c21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 3-Chloroperoxybenzoic acid (1.21 g of 77%, 1.15 eq.) was added in a single portion to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinoline (1.00 g, 4.25 mmol, 1.0 eq) in chloroform (42 mL). The reaction mixture was stirred at ambient temperature for 1 hour at which time analysis by thin layer chromatography ... | C#CCn1c(CC)nc2c[n+]([O-])c3ccccc3c21 | null | 111.4 | null |
627,434 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [CH3:1]C(C)([O-])C.[K+].[CH:7]([C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:28][O:27][C:26]1[CH:25]=[CH:24][C:11]([CH2:12][N:13]2[C:17](=[O:18])[C:16]3... | COc1ccc(CN2C(=O)c3ccccc3C2=O)cc1C=O | CC(C)(C)[O-] | null | C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | [Br-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 3.99 g of potassium-t-butoxide was added to 80 ml solution of 12.7 g methyltriphenyl phosphonium bromide in tetrahydrofuran at 0° C., 7 g of N-(3-formyl-4-methoxybenzyl)phthalimide was added thereto, and the mixture was stirred at room temperature for 1 hr. The reaction solution was filtered through Celite, and then ev... | C=Cc1cc(CN2C(=O)c3ccccc3C2=O)ccc1OC | null | 39.5 | null |
1,733,457 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:14])=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.CCN(C(C)C)C(C)C.[CH3:40][N:41]1[CH2:45][CH2:44][C:43]2([CH2:49][CH2:48][NH:47][CH2:46]2)[CH2:42]1>C(Cl)Cl>[Cl:1][C:2]1[C... | CN1CCC2(CCNC2)C1 | COc1ccc(CNc2nc(S(C)=O)ncc2C(=O)NCc2ncccn2)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | null | 8 | In DCM (30 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (429 mg, 0.96 mmol) and DIEA (0.22 mL, 1.12 mmol). 2-Methyl-2,7-diazaspiro[4.4]nonane (154 mg, 1.1 mmol) was then added. The reaction was conducted at ambient temperature overnight. The so... | COc1ccc(CNc2nc(N3CCC4(CCN(C)C4)C3)ncc2C(=O)NCc2ncccn2)cc1Cl | null | 4 | null |
215,556 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | [CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].C(N(C(C)C)C(C)C)C.C1(C)C=CC(S(O[CH2:31][CH2:32][CH:33]2[CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[O:35][CH2:34]2)(=O)=O)=CC=1>CN(C)C=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:31][CH2:32][CH:33]2[CH2:42][C:41]... | CCOC(=O)C1CCCNC1 | Cc1ccc(S(=O)(=O)OCCC2COc3ccccc3C2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 16 | First 3.76 g (24 mmol) of piperidine-3-carboxylic acid ethyl ester and then 3.1 g (24 mmol) of N-ethyl-N,N-diisopropylamine are added to a solution of 3.98 g (12 mmol) of 3-[2-(p-toluenesulphonyloxy)ethyl]chroman in 50 ml of absolute dimethylformamide. The mixture is stirred for 16 hours at 60° and, after cooling, is c... | CCOC(=O)C1CCCN(CCC2COc3ccccc3C2)C1 | null | 97.1 | null |
1,372,229 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH3:1][C:2]1[N:6]=[C:5]([C@H:7]([NH:9]C(=O)OC(C)(C)C)[CH3:8])[O:4][N:3]=1.Cl>O1CCOCC1>[CH3:1][C:2]1[N:6]=[C:5]([C@H:7]([NH2:9])[CH3:8])[O:4][N:3]=1 | Cc1noc([C@@H](C)NC(=O)OC(C)(C)C)n1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 16 | To a solution of tert-butyl [(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]carbamate (6.0 g, 26.4 mmol) in dioxane (40 mL) was added 4 M hydrochloric acid in dioxane (30 mL). The reaction mixture was stirred for 16 h. The solution was concentrated and dried by vacuum to give hydrochloride salt of (1R)-1-(3-methyl-1,2,4-o... | Cc1noc([C@@H](C)N)n1 | null | 151.9 | null |
1,147,163 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([B:16]4[O:20]C(C)(C)C(C)(C)[O:17]4)=[CH:12][N:11]3[CH:25]=2)=[CH:4][CH:3]=1.Cl>CC(C)=O.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([B:16]([OH:20])[OH:17])=[CH:12][N:11]3[CH:25]=2)=[CH:6][CH:7]=1 | CC1(C)OB(c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)OC1(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | O | null | null | null | null | null | null | null | null | null | null | null | 7.93 g of 2-(4-chlorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine are dissolved in 200 ml of acetone and 100 ml of water; 223 ml of 1N hydrochloric acid are added thereto, dropwise there with stirring, and the mixture is stirred at ambient temperature for 16 h. The reaction mixture is s... | OB(O)c1ccc2nc(-c3ccc(Cl)cc3)cn2c1 | null | 138.4 | null |
1,379,268 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([NH:11][C:12]2[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][N:24](COCC[Si](C)(C)C)[C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[C:14](S(C)(=O)=O)[N:13]=2)[CH2:6]1)(=[O:4])=[O:3].[C:39](#[N:41])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([... | CC#N | C[Si](C)(C)CCOCn1ccc2nc(-c3cnc(S(C)(=O)=O)nc3N[C@H]3CCCN(S(C)(=O)=O)C3)cnc21 | null | CCCC[N+](CCCC)(CCCC)CCCC | [C-]#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of ((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methanesulfonyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine derived from Example 84, step 1 was treated with tetra-n-butyl ammonium cyanide in acetonitrile at 100° C. for 4 hours. Solvent was concentrated to dryness ... | CS(=O)(=O)N1CCC[C@H](Nc2nc(C#N)ncc2-c2cnc3[nH]ccc3n2)C1 | null | null | null |
84,743 | ord_dataset-50c29bf1847c44f4b40bfab5f46fe5fe | null | 1981-01-01T00:08:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C:10]([C:13]2[CH:18]=[C:17]([Br:19])[C:16]([OH:20])=[C:15]([Br:21])[CH:14]=2)([CH3:12])[CH3:11])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].[CH2:22]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:23]1[O:25][CH2:24]1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH2:27]([O:26][CH2:22][CH:23]([OH:25])[CH2:24][O:8][C:7]1[C... | CCCCOCC1CO1 | CC(C)(c1cc(Br)c(O)c(Br)c1)c1cc(Br)c(O)c(Br)c1 | null | C[N+](C)(C)Cc1ccccc1 | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane (i.e., tetrabromobisphenol A) (136 g; 0.25 mole), butyl glycidyl ether having an epoxide content of 7.45 equiv./kg (67.1 g; 0.5 equiv.), and benzyltrimethylammonium chloride (0.5 g) were stirred at 120° C. for 1 hour and at 150° C. for 41/2 hours. The mixture had a residual e... | CCCCOCC(O)COc1c(Br)cc(C(C)(C)c2cc(Br)c(OCC(O)COCCCC)c(Br)c2)cc1Br | null | null | null |
1,763,319 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7](B(O)O)[C:6]([O:12][CH3:13])=[CH:5][N:4]=1.[F:14][CH:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1Br)[F:16]>>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH:15]([F:14])[F:16])=[C:19]([C:7]2[C:6]([O:12][CH3:13])=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:20]=1 | FC(F)Oc1ccc(Cl)cc1Br | COc1cc(B(O)O)c(OC)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 417 mg (2.19 mmol, 1.2 eq.) of 2,5-dimethoxypyridin-4-ylboronic acid and 494 mg (1.82 mmol) of 2-bromo-4-chlorophenyl difluoromethyl ether in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were reacted according to General Method 2A. The crude product was purified... | COc1cc(-c2cc(Cl)ccc2OC(F)F)c(OC)cn1 | null | null | null |
1,562,114 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH2:13][C:14](=[O:34])[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]([CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[C:25]([O:27]C)=[O:26])=[CH:20][CH:19]=3)[N:16]=2)=[CH:7][CH:6]=1>O1CCOCC1.O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH2:13][C:14](=[O:34]... | COC(=O)C(c1ccc(CN2N=C(c3ccc(Cl)cc3)OCC2=O)cc1)C1CCCC1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 80 | 12 | 86 mg (2.04 mmol) of lithium hydroxide monohydrate were added to a solution of 450 mg (1.02 mmol) of methyl (4-{[2-(4-chlorophenyl)-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl]methyl}phenyl)(cyclopentyl)acetate in 10 ml of dioxane and 10 ml of water, and the mixture was stirred at 80° C. for 12 h. After removal of the di... | O=C(O)C(c1ccc(CN2N=C(c3ccc(Cl)cc3)OCC2=O)cc1)C1CCCC1 | null | null | null |
393,427 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [CH2:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>>[CH2:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][Br:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | Nc1ccccc1Cc1ccccc1 | O=C(Cl)CCCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-benzylaniline and 4-bromobutyryl chloride were used to produce the above compound in the same way as Reference Example 8. | O=C(CCCBr)Nc1ccccc1Cc1ccccc1 | null | null | null |
1,373,589 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [NH:1]([CH2:6][CH2:7][C:8]#[N:9])[CH2:2][CH2:3][C:4]#[N:5].N[NH:11][C:12]([NH2:14])=[S:13].O.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[NH2:11][C:12]1[S:13][C:4]([CH2:3][CH2:2][NH:1][CH2:6][CH2:7][C:8]2[S:13][C:12]([NH2:14])=[N:11][N:9]=2)=[N:5][N:14]=1 | N#CCCNCCC#N | NNC(N)=S | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | O | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 3,3′-iminodipropionitrile (1.50 g, 12.18 mmol) and thiosemicarbazide (2.22 g, 24.36 mmol) in TFA (10 mL) was heated at 85 for 4.5 h. The reaction was cooled to room temperature and poured into a mixture of ice and water. Sodium hydroxide pellets were added to the mixture until it was basic (pH 14). The whi... | Nc1nnc(CCNCCc2nnc(N)s2)s1 | null | 44.5 | null |
634,818 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | O.[C:2]1([C:8]([CH:10]=[O:11])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:12]C1C=CC(C(=O)C)=CC=1>>[OH2:9].[F:12][C:5]1[CH:6]=[CH:7][C:2]([C:8]([CH:10]=[O:11])=[O:9])=[CH:3][CH:4]=1 | O=CC(=O)c1ccccc1 | CC(=O)c1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared using essentially the same procedure as described by H. A. Riley and A. R. Gray in Organic Synthesis, Collective Volume II, p. 509 for the preparation of phenylglyoxal hydrate, but using 4′-fluoroacetophenone in place of acetophenone. | O=CC(=O)c1ccc(F)cc1 | null | null | null |
528,584 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]3[CH2:24][CH2:25][CH:19]2[C:20](=[O:26])[O:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C.CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]3[CH2:24][CH2:25][CH:19]2[C:20](=[O:26])[O:21]3)(=[O:17])=[O:16])=[CH:1... | O=C1OC2CCC1N(S(=O)(=O)c1ccc(OCc3ccccc3)cc1)C2 | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-(4-benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (1.0 g, 2.7 mmol), ethyl acetate-methanol (1:1, 100 mL) and 10% Pd on charcoal (0.22 g) was shaken under 50 psi of hydrogen for 1.5 h. Filtration through a pad of Celite and concentration of the filtrate in vacuo afforded 0.80 g of 5-(4-... | O=C1OC2CCC1N(S(=O)(=O)c1ccc(O)cc1)C2 | null | 104.6 | null |
793,245 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | Cl.[OH:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[Br:8].[CH3:9][N:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11](Cl)=[O:12]>>[Br:8][C:4]1[N:3]([O:2][C:11](=[O:12])[N:10]([CH3:9])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][N:5]=1 | On1ccnc1Br | CN(C(=O)Cl)c1ccccc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 1-hydroxy-2-bromoimidazole, hydrochloride and N-methyl-N-phenylcarbamoyl chloride applying the general procedure 8. The crude product was purified by flash chromatography (Quad flash 12, EtOAc-heptane) (63%, oil). | CN(C(=O)On1ccnc1Br)c1ccccc1 | null | null | null |
960,576 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [C:1]([C:3]1[CH:4]=[N:5][N:6]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:8][C:7]=12)#[CH:2].Br[C:27]1[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[N:31][CH:32]=1>>[F:15][C:12]([F:14])([F:13])[C:11]1[N:6]2[N:5]=[CH:4][C:3](... | C#Cc1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1cncc(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 3-ethynyl-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.1) (355 mg, 1.0 mmol) and 5-bromo-pyridine-3-sulfonic acid amide (example B.1) (356 mg, 1.5 mmol) according to general procedure II. Obtained as a yellow solid (90 mg, 18%). MS (ISP) 512.3 ... | NS(=O)(=O)c1cncc(C#Cc2cnn3c(C(F)(F)F)cc(-c4ccc(C(F)(F)F)cc4)nc23)c1 | null | null | null |
802,672 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])[C:10]=3[N:11]=[C:12](S(C)(=O)=O)[N:13]=2)=[C:4]([CH3:30])[CH:3]=1.[F:31][C:32]([F:36])([F:35])[CH2:33][NH2:34]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N... | NCC(F)(F)F | Cc1cc(F)ccc1-c1nc(S(C)(=O)=O)nc2c1ccc(=O)n2-c1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the general procedure outlined in Example 126, the product of Example 121 (150 mg, 0.35 mmol), 2,2,2-trifluoro-ethylamine (176 mg, 1.77 mmol) were reacted to give the crude material, which was purified as described in Example 198 to give the desired product 130 mg (84%). LC-MS: 443.0 (MH+, m/z), 2.27 (Rt, min... | Cc1cc(F)ccc1-c1nc(NCC(F)(F)F)nc2c1ccc(=O)n2-c1ccccc1C | null | 84 | null |
719,565 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [OH:1][C:2]1([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37]Cl)=[CH:28][CH:27]=2)[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][O:14][CH3:15])=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:18][CH:17]=1.[I-:39].[Na+]>CC(=O)CC.[I-].C([N+](CCCC)(CCCC)... | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCCl)cc2)cc1 | [I-] | null | CCCC[N+](CCCC)(CCCC)CCCC | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | 4-Hydroxy-4-{4-[2-(2-chloroethoxy)ethoxy]phenyl}-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman (490 mg, 0.9 mmol) was dissolved in 2-butanone (30 ml) under argon atmosphere. Then, sodium iodide (1.4 g, 9.3 mmol) and tetrabutylammonium iodide (1.6 g, 4.5 mmol) were added thereto, and the mixture was refluxed fo... | COCOc1ccc(C2COc3cc(OCOC)ccc3C2(O)c2ccc(OCCOCCI)cc2)cc1 | null | 92 | null |
394,494 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [NH:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3].Cl[CH2:15][CH2:16][CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])(=[O:23])[O:20][CH2:21][CH3:22]>>[CH3:5][N:4]1[C:6]2[N:7]=[CH:8][N:9]([CH3:10])[C:11]=2[C:12](=[O:13])[N:1]([CH2:15][CH2:16][CH2:17][CH2:18][P:19](=[O:23])([O:24][CH2... | CCOP(=O)(CCCCCl)OCC | Cn1cnc2c1c(=O)[nH]c(=O)n2C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title substance was prepared from 0.075 mol of theobromine and 0.09 mol of diethyl 4-chlorobutanephosphonate analogously to Example 23 and crystallized from diisopropyl ether. | CCOP(=O)(CCCCn1c(=O)c2c(ncn2C)n(C)c1=O)OCC | null | null | null |
889,584 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [I:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6]2.FC(F)(F)C(O)=O>>[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][CH2:6]2 | Ic1cccc2c1CN(C(c1ccccc1)(c1ccccc1)c1ccccc1)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogy to Example A2(c) from 4-Iodo-2-trityl-2,3-dihydro-1H-isoindole and trifluoroacetic acid. Light yellow solid. | Ic1cccc2c1CNC2 | null | null | null |
1,514,429 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH:1]1([CH2:4][C:5](=[O:20])[CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:8]=2)[CH2:3][CH2:2]1.[CH3:21][N:22]([CH:24](OC)OC)[CH3:23]>>[CH:1]1([CH2:4][C:5](=[O:20])/[C:6](/[C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:8]=2)=[... | COC(OC)N(C)C | O=C(Cc1ccnc(Nc2ccncc2)n1)CC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 80 | 0.5 | 1-Cyclopropyl-3-[2-(pyridin-4-ylamino)pyrimidin-4-yl]propan-2-one (8) (269 mg, 1.003 mmol) was taken up in DMF-DMA (5.369 mL, 40.1 mmol) and stirred at 80° C. for 30 minutes. The solvent was evaporated and the residue partitioned between DCM and water. The organic layer was washed with saturated sodium bicarbonate and ... | CN(C)/C=C(\C(=O)CC1CC1)c1ccnc(Nc2ccncc2)n1 | null | 98.7 | null |
1,477,302 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.[H-].[Na+].[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:35]Br>CN(C=O)C.C(OCC)(=O)C>[F:31][C:32]1[CH... | Fc1ccc(CBr)cc1F | CCOC(=O)C1CCCn2c(-c3ccc(-c4cnc(C)o4)c(OC)c3)nnc21 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0.5 | Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (3.00 g) was added to a suspension of sodium hydride (60%, 340 mg) in DMF (5 mL) under ice-cooling. The reaction mixture was stirred for 30 min under ice-cooling, 3,4-difluorobenzyl bromide (1.53 g) was... | CCOC(=O)C1(Cc2ccc(F)c(F)c2)CCCn2c(-c3ccc(-c4cnc(C)o4)c(OC)c3)nnc21 | null | 92.3 | null |
434,846 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][C:12](=[O:15])[CH2:13]Br)[CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C=O)C.[OH-].[K+]>CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][C:12](=[O:15])[CH2:13][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][... | Nc1ccccc1 | O=C(CBr)Nc1cc(Cl)ccc1C(=O)O | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 20 | A solution of 4-chloro-2-(bromoacetamido)benzoic acid from Example 40 (6.5 g, 0.02 mol), aniline (5.2 mL, 250 mol %) and anhydrous DMF (50 mL) was heated to 100-105° C. for 4 h, and stirred at rt for 20 h. The reaction mixture was poured into ice-water (400 mL) and the precipitated product was solubilized by adding aqu... | O=C(CNc1ccccc1)Nc1cc(Cl)ccc1C(=O)O | null | 40 | null |
1,314,732 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | Cl.[NH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][N:15]([C:19]([O:21][CH:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[O:20])[CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[C:5]([N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)[N:4]=1>O1CCOCC1.CO>[NH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:18]... | CN1CCN(c2cc(-c3ccc4c(c3)CN(C(=O)OC3CCN(C(=O)OC(C)(C)C)CC3)CC4)nc(N)n2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 25 | 2 | 4 mL of 4 N HCl in 1,4-dioxane was added to a solution of 1-(tert-butoxycarbonyl)piperidin-4-yl 7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.10 g, 0.18 mmol) in methanol (1.0 mL). The reaction mixture was stirred at r.t. for 2 h. The volatiles were removed under redu... | CN1CCN(c2cc(-c3ccc4c(c3)CN(C(=O)OC3CCNCC3)CC4)nc(N)n2)CC1 | null | null | null |
1,719,536 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:13]3=[N:14][C:15]([C:18]4[O:22][C:21]([NH2:23])=[N:20][N:19]=4)=[CH:16][CH:17]=[C:12]3[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=2)[CH:6]=[N:7][CH:8]=1.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:13]3=[N:14][C:15]([C:18]4[O:22][C:21]([NH2:23])=[N:20][N:19]=4)=[CH:16][CH:1... | COc1cncc(-c2cn(S(=O)(=O)c3ccc(C)cc3)c3ccc(-c4nnc(N)o4)nc23)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 5-(3-(5-methoxypyridin-3-yl)-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-1,3,4-oxadiazol-2-amine (0.022 g, 0.048 mmol) and 1 M NaOH (aq.) (0.095 mL, 0.095 mmol) in 4 mL of EtOH was stirred overnight at RT. The reaction was then concentrated and the residue taken up in H2O and EtOAc. The EtO... | COc1cncc(-c2c[nH]c3ccc(-c4nnc(N)o4)nc23)c1 | null | 14.9 | null |
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