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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
136,466 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | Br.Br[CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([NH:12][C:13]([NH2:15])=[NH:14])=[N:9][C:8]=2[CH:16]=1.[Na]>>[NH2:9][CH2:8][CH2:7][S:11][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([NH:12][C:13]([NH2:15])=[NH:14])=[N:9][C:8]=2[CH:16]=1 | N=C(N)Nc1nc2cc(CBr)ccc2s1 | null | null | Br | [Na] | 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 | 25 | null | Cysteamine.hydrochloride (0.4 g) was caused to react with sodium ethoxide in ethanol to yield a sodium salt. Then, 5-bromomethyl-2-guanidinobenzothiazole.hydrobromide (0.63 g) was added to the sodium salt at an internal temperature of 0° C. After agitating the mixture over one night at room temperature, the solvent was... | N=C(N)Nc1nc2cc(CSCCN)ccc2s1 | null | null | null |
668,408 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | [Si]([O:8][C@H:9]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:26]([CH3:34])([CH2:27][CH2:28][C:29]=32)[C@@H:18]([C@H:19]([CH3:25])[CH2:20][CH2:21][C:22]([OH:24])=O)[CH2:17][CH:16]=4)[C:10]1([CH3:36])[CH3:35])(C(C)(C)C)(C)C.[C:37]([NH2:41])([CH3:40])([CH3:39])[CH3:38].Cl.C(O)C>>[C:37](... | C[C@H](CCC(=O)O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]1CC3 | CC(C)(C)N | null | Cl | 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 | null | 3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid (0.50 g) is reacted with tert-butylamine and hydrolysed with HCl/ethanol following the procedure outlined in example 39 to give the title compound (204 mg). Melting point: 171-176° C. | C[C@H](CCC(=O)NC(C)(C)C)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3 | null | null | null |
736,421 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [NH2:1][C:2]1[N:3]=[C:4]([Cl:39])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28]CC4C=CC(Cl)=CC=4Cl)[C@@H:14]([O:15]CC4C=CC(Cl)=CC=4Cl)[C@@:12]3([CH3:38])[OH:13])[C:6]=2[N:7]=1.B(Cl)(Cl)Cl>C(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([Cl:39])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:... | C[C@@]1(O)[C@H](OCc2ccc(Cl)cc2Cl)[C@@H](COCc2ccc(Cl)cc2Cl)O[C@H]1n1ccc2c(Cl)nc(N)nc21 | null | null | ClB(Cl)Cl | null | 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 | -78 | 2 | To a solution of the product from Step A (630 mg, 1.0 mmol) in CH2Cl2 (20 mL) at −78° C. was added boron trichloride (1M in CH2Cl2) (10 mL, 10 mmol). The mixture was stirred at −78° C. for 2 h, then at −20° C. for 2.5 h. The reaction was quenched with CH2Cl2MeOH (1:1) (10 mL), stirred at −20° C. for 0.5 h, and neutrali... | C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(Cl)nc(N)nc21 | null | 79.4 | null |
206,567 | ord_dataset-dd1de64954674e17b4b690cac09dc67b | null | 1990-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:33]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)(=[O:35])[CH3:34]>O1CCCC1>[C:33]([N:36]1[CH2:41][CH2:40][N:39]([C:18](=[O:20])[CH2:17][N:16]2[C:11]3=... | CC(=O)N1CCNCC1 | O=C(O)Cn1c(-c2ccc(Cl)cc2)nc2cccnc21 | null | O=C(n1ccnc1)n1ccnc1 | 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 | 3 | A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.0 g, 0.014 mole), 1,1'-carbonyldiimidazole (2.26 g, 0.014 mole) and dry tetrahydrofuran (80 ml) was stirred at room temperature for 3 hr with a stream of nitrogen bubbling through it. A solution of 1-acetylpiperazine (4.49 g, 0.035 mole) in t... | CC(=O)N1CCN(C(=O)Cn2c(-c3ccc(Cl)cc3)nc3cccnc32)CC1 | null | 57.1 | null |
36,373 | ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a | null | 1978-01-01T00:02:00 | true | N.[CH3:2][C:3]1[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:5][N:6]([CH:8]([CH2:12][CH2:13][CH3:14])[C:9](O)=[O:10])[CH:7]=1.C[CH:22]([N:26]1[CH:30]=C(C)C(C2C=CC=CC=2)=N1)C(O)=O>>[CH3:22][N:26]([CH3:30])[C:9](=[O:10])[CH:8]([CH2:12][CH2:13][CH3:14])[N:6]1[CH:7]=[C:3]([CH3:2])[C:4]([C:15]2[CH:20]=[CH:19][CH:... | CCCC(C(=O)O)n1cc(C)c(-c2ccccc2)n1 | Cc1cn(C(C)C(=O)O)nc1-c1ccccc1 | null | 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 | null | Following the procedure of Example 68, but substituting dimethylamine for aqueous ammonia and 4-methyl-3-phenyl-α-propylpyrazole-1-acetic acid for α,4-dimethyl-3-phenylpyrazole-1-acetic acid, there was obtained N,N,4-trimethyl-3-phenyl-α-propylpyrazole-1-acetamide having a melting point of 84°-86° C. | CCCC(C(=O)N(C)C)n1cc(C)c(-c2ccccc2)n1 | null | null | null |
790,764 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | Br[CH2:2][C:3]([C:5]1[C:10]2[CH2:11][C:12](=[CH:20][CH2:21][CH2:22][Br:23])[C:13]3[C:14]([O:19][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[N:15][CH:16]=[CH:17][CH:18]=3)=O.[NH2:24][C:25]([NH2:27])=[S:26].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:27][C:25]1[S:26][CH:2]=[C:3]([C:5]2[C:10]3[CH2:11][C:12](=[CH:20][CH2:21][CH2:22][Br:23])[C:13]4[C:... | O=C(CBr)c1cccc2c1CC(=CCCBr)c1cccnc1O2 | NC(N)=S | null | O=C([O-])O | [Na+] | 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 | 70 | 0.5 | To a solution of the product of step 1 (1.1 g) in ethanol (11 ml) was added thiourea (193 mg) at room temperature, and the mixture stirred at 70° C. for 30 minutes. The reaction mixture was cooled to room temperature and poured into saturated aqueous sodiumbicarbonate. The aqueous layer was extracted with ethyl acetate... | Nc1nc(-c2cccc3c2CC(=CCCBr)c2cccnc2O3)cs1 | null | 71.8 | null |
676,457 | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | null | 2005-01-01T00:07:00 | true | Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][C:15](=[O:30])[CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)[CH:3]=1.C(N(CC)C(C)C)(C)C.Cl.[NH2:41][CH2:42][C:43]([NH2:45])=[O:44]>>[NH2:45][C:43](=[O:44])[CH2:42][NH:41]... | NCC(N)=O | O=C(CN1CCC(Cc2ccccc2)CC1)Nc1cc(Cl)nc(-c2ccccc2)n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 100 | null | To a crude sample of N-(6-chloro-2-phenylpyrimidin-4-yl)-2-(4-benzylpiperidin-1-yl)acetamide (22.55) (0.75 g in 60 ml DMSO) were added glycinamide hydrochloride (1.85 g in 10 ml DMSO) and N,N-diisopropylethylamine (2.96 ml) and the mixture heated to 100° C. for 16 hrs. The solvent was then removed in vacuo and the resi... | NC(=O)CNc1cc(NC(=O)CN2CCC(Cc3ccccc3)CC2)nc(-c2ccccc2)n1 | null | 39.9 | null |
1,632,481 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1.[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][CH2:20]Br.[OH-].[Na+]>CO>[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][CH2:20][N:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]... | Fc1ccccc1CCBr | COC(=O)c1ccnc(-c2c[nH]cn2)c1 | null | [Na+] | [OH-] | 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 | The title compound was prepared in 48% yield from methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 5) and 2-fluorophenethyl bromide according to the procedure for the preparation of Example 44, followed by saponification using NaOH in MeOH. 1HNMR (400 MHz, DMSO): δ 3.14 (2H, t, J=6.9 Hz), 4.29 (2H, t, J=7... | O=C(O)c1ccnc(-c2cn(CCc3ccccc3F)cn2)c1 | null | 48 | null |
1,010,942 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]([Cl:16])[C:6]=2[N:7]=1.C(N(C(C)C)C(C)C)C.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:5]2[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C... | COC(=O)c1cc(Cl)c2nc(Cl)nc(Cl)c2n1 | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 0 | 0.25 | To a solution of methyl 2,4,8-trichloropyrido[3,2-d]pyrimidine-6-carboxylate (4.65 g; 15.9 mmol; 1 eq.) (Intermediate 1.3) in acetonitrile (140 mL) was added N-ethyldiisopropyl amine (4 mL; 23.8 mmol; 1.5 eq.). The mixture was cooled down to 0° C. A solution of piperidine (1.57 mL; 15.9 mmol; 1 eq.) in acetonitrile (20... | COC(=O)c1cc(Cl)c2nc(Cl)nc(N3CCCCC3)c2n1 | null | 73.4 | null |
972,948 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [N:1]1([C:5]([C:7]2[CH:41]=[CH:40][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:25]=[C:26]([O:28][C@@H:29]([CH3:39])[CH2:30][O:31][Si](C(C)(C)C)(C)C)[CH:27]=3)[C:15]([NH:17][C:18]3[CH:23]=[N:22][C:21]([CH3:24])=[CH:20][N:19]=3)=[O:16])=[C:9]([F:42])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1>CO.Cl>[N:1]1([C:5]([C:7]2[CH:41]=[CH:40... | Cc1cnc(NC(=O)c2cc(Oc3ccc(C(=O)N4CCC4)cc3F)cc(O[C@@H](C)CO[Si](C)(C)C(C)(C)C)c2)cn1 | null | null | Cl | 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 | 0.5 | A mixture of 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methylpyrazin-2-yl)benzamide (3.6 g, 5.96 mmol) in methanol (60 mL) and 1M hydrochloric acid (60 mL) was stirred for 30 mins at RT. The volatiles were removed in vacuo and the residue adjusted to p... | Cc1cnc(NC(=O)c2cc(Oc3ccc(C(=O)N4CCC4)cc3F)cc(O[C@@H](C)CO)c2)cn1 | null | null | null |
643,726 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [OH:1][N:2]=[C:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:4]#[N:5].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O1CCCC1>[CH3:18][S:19]([O:1][N:2]=[C:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:4]#[N:5])(=[O:21])=[O:20] | CS(=O)(=O)Cl | N#CC(=NO)c1cccs1 | null | null | 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 | 0 | 0.5 | In general analogy to the reaction described under 3.2, 38 g (0.25 mol) of α-hydroxyiminothiophene-2-acetonitrile and 37.95 g (0.375 mol) of triethylamine are dissolved in 350 ml of tetrahydrofuran and to this solution is then added dropwise a solution of 31.5 g (0.275 mol) of methanesulfonyl chloride at 0-5° C. After ... | CS(=O)(=O)ON=C(C#N)c1cccs1 | null | 91 | null |
816,156 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH2:1]([N:3]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33])[C:4](=[O:25])[CH2:5][CH2:6][C:7]1[CH:24]=[CH:23][C:10]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([O:17]C)=[O:16])=[CH:9][CH:8]=1)[CH3:2].[OH-].[K+]>CCO>[CH2:1]([N:3]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F... | CCN(Cc1ccccc1F)C(=O)CCc1ccc(OCc2ccccc2C(=O)OC)cc1 | null | null | [K+] | [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 | Methyl 2-[(4-{3-[ethyl(2-fluorobenzyl)amino]-3-oxopropyl}phenoxy)methyl]-benzoate (0.454 g, 1.001 mmol) was dissolved in EtOH (5 ml) and potassium hydroxide (0.085 g, 1.514 mmol) was added. The reaction was performed in a single node microwave oven (7 min, 150° C.). Workup was by removing the solvent by evaporation, ad... | CCN(Cc1ccccc1F)C(=O)CCc1ccc(OCc2ccccc2C(=O)O)cc1 | null | 18.1 | null |
644,127 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | CN(C)C=O.P(Cl)(Cl)([Cl:8])=O.[CH3:11][O:12][C:13]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35])[C:14]=1[C:15]([C:17]1[C:22]([O:23][CH3:24])=[CH:21][N+:20]([O-])=[CH:19][C:18]=1[Cl:26])=[O:16]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35]... | O=P(Cl)(Cl)Cl | COc1cc(C)c(C(=O)c2c(Cl)c[n+]([O-])cc2OC)c(OC)c1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 5 ml of dimethylformamide was added to 2.5 ml of toluene, the mixture was cooled with ice, and 1.3 ml (1.4 mmol) of phosphorus oxychloride was dropwise added thereto. After the mixture was stirred under cooling with ice for 10 minutes, 2.5 g (0.7 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-... | COc1cc(C)c(C(=O)c2c(OC)cnc(Cl)c2Cl)c(OC)c1OC | null | 739.8 | null |
5,443 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([OH:11])[CH:5]=1)([O-:3])=[O:2].[CH2:12](Br)[CH2:13][CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][CH:14]([CH3:16])[CH2:13][CH2:12][O:11][C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1 | Cc1ccc(O)cc1[N+](=O)[O-] | CC(C)CCBr | null | O=C([O-])[O-] | [K+] | 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 | A mixture of 50 parts of 3-nitro-p-cresol, 94 parts of isoamyl bromide and 94.2 parts of anhydrous potassium carbonate in 650 parts of acetone was stirred and heated under reflux for 18 hours. Insoluble material was filtered off and washed with acetone and the total acetone solution was evaporated. An oil remained whic... | Cc1ccc(OCCC(C)C)cc1[N+](=O)[O-] | null | null | null |
275,531 | ord_dataset-02ee2261663048188cf6d85d2cc96e3f | null | 1993-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>O1CCCC1>[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1)(=[O:22])[CH:20]=[CH2:21] | Cc1nc2cc(N)ccc2o1 | C=CC(=O)Cl | null | null | 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 | 0 | null | About 150 parts of (2) are dissolved in about 1200 ml of warm tetrahydrofuran in a 3 liter three-necked flask equipped with a mechanical stirrer and dropping funnel. About 113 parts of triethylamine are added to the flask and then cooled to 0° C. using an ice bath. About 100 parts of acryloyl chloride are combined with... | C=CC(=O)Nc1ccc2oc(C)nc2c1 | null | null | null |
1,476,269 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[C:16]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)[CH:25]=4)[C:17]4[S:22][CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH:37]O.N>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]... | Clc1ccc(N2CCN(c3nc4c(c(Nc5cccc(CN6CCOCC6)c5)n3)SCC4)CC2)cc1 | OO | null | N | null | 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 | 10 | 0.25 | 313.80 mg {2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl}-(3-morpholin-4-ylmethyl-phenyl)-amine are placed in 2.70 ml glacial acetic acid and cooled to 10° C. 57 μl hydrogen peroxide (35%) are added dropwise, then the mixture is stirred for 0.25 hours. Then the reaction mixture is stirr... | O=S1CCc2nc(N3CCN(c4ccc(Cl)cc4)CC3)nc(Nc3cccc(CN4CCOCC4)c3)c21 | null | null | null |
1,747,516 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[Br:19][C:20]1[CH:46]=[CH:45][C:23]2[N:24]([C:32]([C:34]3[CH:35]=[CH:36][C:37]4[O:42][CH2:41][C:40](=[O:43])[NH:39][C:38]=4[CH:44]=3)=[O:33])[CH:25]([CH2:28][C:29](O)=[O:30])[CH2:26][O:27][C:22]=2[CH:21]=1.[CH3:47][NH2:48].C1COCC1>CCOC(C)=O>[Br:19][C:20]1[CH:46]=[CH:45][C:23]2[N:24](... | CN | O=C(O)CC1COc2cc(Br)ccc2N1C(=O)c1ccc2c(c1)NC(=O)CO2 | null | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.08 | TEA (0.461 mL, 3.33 mmol) and T3P (50 wt. % in EtOAc, 0.989 mL, 1.66 mmol) were added to a solution of {7-bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetic acid (Intermediate 29, 372 mg, 0.83 mmol) in EtOAc (5 mL). The mixture was stirred for 5 min. Methanamine in TH... | CNC(=O)CC1COc2cc(Br)ccc2N1C(=O)c1ccc2c(c1)NC(=O)CO2 | null | 56 | null |
750,103 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([F:16])[CH:3]=1.C([Li])CCC.CN(C)[C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[F:16][C:4]1[CH:3]=[C:2]([C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:7]=[C:6]([CH3:8])[C:5]=1[NH:9][C:10](=[O:... | CCCCCC(=O)N(C)C | Cc1cc(Br)cc(F)c1NC(=O)C(C)(C)C | 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 | 0 | 0.5 | A solution of N-(4-bromo-2-fluoro-6-methylphenyl)-2,2-dimethylpropanamide (21.7 g, 79.2 mmol) in anhydrous tetrahydrofuran (500 mL) was placed under a nitrogen atmosphere, cooled in a dry ice-acetone bath, and stirred while butyllithium (124 mL of a 1.6M solution in hexanes, 198 mmol) was added dropwise. The resulting ... | CCCCCC(=O)c1cc(C)c(NC(=O)C(C)(C)C)c(F)c1 | null | 52.2 | null |
272,322 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | [CH:1]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH:1]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:19][C:20]3[CH:29]=[CH:28][C:... | ClCc1ccc2ccccc2n1 | O=C(c1ccc(O)cc1)C1CCCCCC1 | 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 | In analogy to the procedure of Example III, the title compound is prepared from 10 g (45.8 mmol) of the compound from Example XII, 10.3 g (48.1 mmol) of 2-chloromethylquinoline hydrochloride and 13.8 g (0.10 mol) of potassium carbonate. | O=C(c1ccc(OCc2ccc3ccccc3n2)cc1)C1CCCCCC1 | null | null | null |
908,534 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH:29]=[C:28](O)[CH:27]=[CH:26]3)=[CH:19][CH:18]=1>ClCCl.N1C=CC=CC=1>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[CH:31][CH:32]=[C:23... | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | Oc1ccc2cc(-c3ccc(F)cc3)ccc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 1 | Trifluoromethanesulfonic anhydride (1.3 mL, 7.74 mmol) was added over 5 minutes to a stirred solution of 6-(4-fluorophenyl)-2-naphthol (Step 1, 1.75 g, 7.35 mmol) in dichloromethane (25 mL) and pyridine (15 mL) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 hour then allowed to warm to room temperatur... | O=S(=O)(Oc1ccc2cc(-c3ccc(F)cc3)ccc2c1)C(F)(F)F | null | 86 | null |
1,748,745 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:16]=1[N+:25]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:25][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([C:21]([F:22])([F:23])[F:24])[C:15]=1[O:14][CH2:13][C@H:9]([NH:8][C:6]([O:5... | CC(C)(C)OC(=O)N[C@@H](COc1c([N+](=O)[O-])cccc1C(F)(F)F)C(=O)O | null | 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 | null | null | 10% Pd/C (150 mg) was added to a solution of (S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-6-(trifluoromethyl)phenoxy)propanoic acid (1.5 g, 3.8 mmol) in MeOH and the mixture stirred under H2. After 4 h the mixture was filtered through Celite, the filter cake washed with MeOH and the filtrate concentrated to afford (S)-3... | CC(C)(C)OC(=O)N[C@@H](COc1c(N)cccc1C(F)(F)F)C(=O)O | null | 88.8 | null |
1,557,097 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl[C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:19]=[C:13]3[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][N:12]3[N:11]=2)[C:5](=[O:8])[NH:6][N:7]=1.[C:20]([C:24]1[S:31][C:30]2[C:29](=[O:32])[N:28]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35](B4OC(C)(C)C(C)(C)O4)[C:34]=3[CH3:48])[CH2:27][C:26]=2[CH:25]=1)([CH3:23])([CH3:22])[CH3:21].O1CCOCC1.C... | Cc1c(B2OC(C)(C)C(C)(C)O2)cccc1N1Cc2cc(C(C)(C)C)sc2C1=O | CN1CCn2nc(Nc3cc(Cl)n[nH]c3=O)cc2C1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | In a dried pressure flask was placed 0.968 mmol of 101m, 1.065 mmol of 101g, and 56 mg (5 mol %) of tetrakis(triphenylphosphine)palladium(0), The flask was evacuated under vacuum, then filled with nitrogen. This procedure was repeated twice more, then 8 mL of anhydrous dioxane and 2.4 mL (2.5 equivalents) of 1 M aqueou... | Cc1c(-c2cc(Nc3cc4n(n3)CCN(C)C4)c(=O)[nH]n2)cccc1N1Cc2cc(C(C)(C)C)sc2C1=O | null | null | null |
1,246,554 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2] | Nc1ccccc1 | O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1 | null | O=C([O-])[O-] | [K+] | 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 | 50 | null | To 3-nitrobenzene-1-sulfonyl chloride (296.9 mg, 1.340 mmol) is added THF (20 mL), aniline (134.8 mg, 1.447 mmol) and potassium carbonate (408.5 mg, 2.955 mmol). The resulting mixture is heated at 50° C. for 16 hours. The reaction mixture is subsequently cooled and concentrated in vacuo after which the residue is treat... | O=[N+]([O-])c1cccc(S(=O)(=O)Nc2ccccc2)c1 | null | 68.9 | null |
1,732,609 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH:1]([Si:4]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:17]3[CH:18]=[C:19]([O:22][C@H:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C@@H:26]([NH2:33])[CH2:25][CH2:24]4)[CH:20]=[CH:21][C:16]3=[N:15][N:14]=2)[CH2:9][CH2:8]1)([CH3:3])[CH3:2].ClC(Cl)(Cl)C... | CC(C)(C)c1cc(NC(=O)OCC(Cl)(Cl)Cl)no1 | CC(C)[Si](OCC1CCN(c2nnc3ccc(O[C@@H]4CC[C@H](N)c5ccccc54)cn23)CC1)(C(C)C)C(C)C | 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 14e was reacted with (5-tert-butyl-isoxazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (WO 2006/091671, which is incorporated herein by reference in its entirety) in an analogous manner to that described in Example 14 step f to give the title compound. LCMS (Method 3): Rt: 5.43 min, m/z 717 [MH+]. | CC(C)[Si](OCC1CCN(c2nnc3ccc(O[C@@H]4CC[C@H](NC(=O)Nc5cc(C(C)(C)C)on5)c5ccccc54)cn23)CC1)(C(C)C)C(C)C | null | null | null |
918,576 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | C(CC1C=CC(C[CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[CH:21]2[CH2:30][CH2:29][C:28]3[CH:27]=[C:26]([O:31]C(=O)C(C)(C)C)[CH:25]=[CH:24][C:23]=3[CH2:22]2)=CC=1)(O)=O.[NH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH2:11]([N:12]([CH2:27][C:28]1[CH:29]=[CH:30][C:21]([CH2:14][CH... | COc1ccc(C2CCc3cc(OC(=O)C(C)(C)C)ccc3C2)c(NCCCc2ccc(CC(=O)O)cc2)c1 | C1CCNCC1 | 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 | Synthesized from pivalic acid 6-{2-[(4-carboxymethylbenzyl)ethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (27 mg) and piperidine (14 mg) according to an analogous synthetic method to Example 715 and purified by LC-MS, the title compound (6.6 mg) was obtained. | CCN(Cc1ccc(CCN2CCCCC2)cc1)c1cc(OC)ccc1C1CCc2cc(O)ccc2C1 | null | 51.9 | null |
1,611,019 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[S:12][CH:13]=[C:14]([Br:16])[N:15]=1>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=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([C:11]2[S:12][CH:13]=[C:14]([Br:16])[N:15]=2)[C... | OB(O)c1ccccc1 | Brc1csc(Br)n1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)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 | 25 | null | A flask containing 238 mg of tetrakis(triphenylphosphine)palladium, 0.55 g of phenylboronic acid, and 1.00 g of 2,4-dibromothiazole was purged with nitrogen and then charged with 30 ml of toluene, 6.1 ml of ethanol, and 9.1 ml of a 2 M aqueous solution of sodium carbonate, and the mixture was stirred under reflux for 6... | Brc1csc(-c2ccccc2)n1 | null | 71.8 | null |
75,983 | ord_dataset-8868acadaee548d5802e504148fc3b63 | null | 1981-01-01T00:01:00 | true | [CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=2[O:19]C)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I.Br>C(O)(=O)C>[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:12]=[CH:11][C:10]=2[OH:19])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1 | COc1ccc(C(C)(C)C)cc1C(=O)C1CCCCC1 | null | null | Br | I | 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 | 0 | null | To 1.70 g of 2-cyclohexylcarbonyl-4-tert-butylanisole [prepared in Reference Example 2 (a)] dissolved in 10 ml of glacial acetic acid were added 1.0 ml of 57% hydroiodic acid and 2.0 ml of 47% hydrobromic acid, and heated at reflux for 2 hours. The reaction mixture was poured into 50 ml of ice-water, extracted with die... | CC(C)(C)c1ccc(O)c(C(=O)C2CCCCC2)c1 | null | 95.5 | null |
1,387,193 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Br:1][C:2]1[C:3]([NH:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]2)=[N:4][C:5]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])=[N:6][C:7]=1[CH3:8].[H-].[Na+].[CH3:26]I>O1CCCC1>[Br:1][C:2]1[C:3]([NH:16][C@H:17]2[CH2:18][CH2:19][C@H:20]([O:23][CH3:26])[CH2:21][CH2:22]2)=[N:4][C:5]([N:9]2[C:13]([C... | CI | Cc1nc(-n2c(C)ccc2C)nc(N[C@H]2CC[C@H](O)CC2)c1Br | 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 | 0 | 0.67 | To a cooled (0° C.) solution of trans-4-(5-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-ylamino)cyclohexanol (1.45 g, 3.82 mmol) in tetrahydrofuran (40 mL) was added sodium hydride (60% dispersion in oil, 459 mg, 11.5 mmol). After 40 minutes, methyl iodide was added (262 uL, 4.21 mmol) and the mixture was ... | CO[C@H]1CC[C@H](Nc2nc(-n3c(C)ccc3C)nc(C)c2Br)CC1 | null | null | null |
1,412,287 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | CC1C=CC(S([O:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)(=O)=O)=CC=1.[CH3:31][O:32][CH:33]1[CH2:37][O:36][CH2:35][CH:34]1O>>[CH3:31][O:32][C@H:33]1[CH2:37][O:36][CH2:35][C@H:34]1[O:11][CH2:12][CH2:13][O:14][CH:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1 | Cc1ccc(S(=O)(=O)OCCOC2CCN(C(=O)OCc3ccccc3)CC2)cc1 | COC1COCC1O | 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 benzyl 4-(2-{[(4-methylphenyl)sulfony]oxy}ethoxy)piperidine-1-carboxylate (2.50 g, 5.77 mmol) produced in Reference Example 1 (1c) and 4-methoxytetrahydrofuran-3-ol (820 mg, 6.94 mmol), the desired title compound (1.20 g, yield 85%) was obtained by the same method as in Reference Examples 1 (1d) and 1 (1e). | CO[C@H]1COC[C@H]1OCCOC1CCNCC1 | null | 84.8 | null |
1,087,658 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH2:1]([C:5]1[CH2:9][CH2:8][C:7](=[N:10][OH:11])[C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=1)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl.CCCCCC>[CH2:1]([C:5]1[CH2:9][CH2:8][C:7](=[N:10][OH:11])[C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=1)[CH2:2][CH2:3][CH3... | CCCCC1=C(c2ccc(OC)c(F)c2)C(=NO)CC1 | null | null | BrB(Br)Br | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCCCCC | null | null | null | null | null | null | null | null | null | null | 2 | To a stirred solution of 20 mg 3-butyl-2-(3-fluoro-4-methoxyphenyl)-2-cyclopenten-1-one oxime (Example 40) in 5 ml dichloromethane, was added 0.5 ml 1.0 M boron tribromide in hexane at 0° C. under inert atmosphere. The reaction mixture was stirred for 2 hours, poured into saturated aqueous sodium bicarbonate, and extra... | CCCCC1=C(c2ccc(O)c(F)c2)C(=NO)CC1 | null | 57.9 | null |
708,852 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | COC(=O)[C@@H](N)C[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8](CC2C=C(Cl)C=C(Cl)C=2)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7]1 | COC(=O)[C@@H](N)Cc1cn(Cc2cc(Cl)cc(Cl)c2)c2ccccc12 | 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 | (S)-2-tert-Butoxycarbonylamino-3-[1-(3,5-dichloro-benzyl)-1H-indol-3-yl]-propionic acid methyl ester. To a stirring suspension of potassium hydride (0.46 g, 30 wt % in mineral oil, 3.45 mmol) in tetrahydrofuran (4 mL) at −50° C. was added a solution of (S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid met... | c1ccc2[nH]ccc2c1 | null | null | null |
1,657,743 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:17]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:10]([CH3:17])[C:11](=[O:13])[CH3:12])[CH3:9])[CH:5]=[N:6][CH:7]=1 | CC(=O)N[C@H](C)c1cncc(Br)c1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 18 | To a vial is added N-[(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-acetamide (111 mg, 0.46 mmol) in 3 ml of THF, followed by the addition of 60% NaH (35 mg, 0.92 mmol). Then iodomethane (130 mg, 0.91 mmol) is added. The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is diluted with DCM, washe... | CC(=O)N(C)[C@H](C)c1cncc(Br)c1 | null | 87.1 | null |
728,745 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([CH:26]=1)[NH2:25].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Cl:15][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:25][C:24]3[CH:26]=[C:20]([O:19][CH3:18]... | COc1ccc(C)c(N)c1 | N#Cc1cnc2cc(Cl)c([N+](=O)[O-])cc2c1Cl | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CCOCCO | null | null | null | null | null | null | null | null | null | 115 | null | A mixture of 0.9 g (3.36 mmol) of 4,7-dichloro-6-nitro-3-quinolinecarbonitrile, 0.55 g (4.0 mmol) of 5-methoxy-2-methylaniline, 0.46 g (4.0 mmol) of pyridine hydrochloride in 10.0 mL of 2-ethoxyethanol is heated at 115° C. for 1 hour, cooled and poured into a saturated solution of sodium bicarbonate. The oil is extract... | COc1ccc(C)c(Nc2c(C#N)cnc3cc(Cl)c([N+](=O)[O-])cc23)c1 | null | 62.1 | null |
1,099,317 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.[CH3:22][N:23]([CH3:33])[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>>[CH3:22][N:23]([CH3:33])[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:2... | CN(C)c1cccc(C(=O)Cl)c1 | O=C1C(=O)c2ccccc2C2=C1SCC1(CCNCC1)O2 | 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 | Compound 46 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, 3-(dimethylamino)benzoyl chloride and conditions outlined in procedure N. M.p.=170-172° C.; LCMS: 449 [M+H]. | CN(C)c1cccc(C(=O)N2CCC3(CC2)CSC2=C(O3)c3ccccc3C(=O)C2=O)c1 | null | null | null |
1,364,786 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | O=P(Cl)(Cl)Cl.[Br:6][C:7]1[CH:8]=[N:9][C:10]2[N:11]([N:13]=[C:14]([CH3:16])[CH:15]=2)[CH:12]=1.CN([CH:20]=[O:21])C>>[Br:6][C:7]1[CH:8]=[N:9][C:10]2[N:11]([N:13]=[C:14]([CH3:16])[C:15]=2[CH:20]=[O:21])[CH:12]=1 | CN(C)C=O | Cc1cc2ncc(Br)cn2n1 | 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 | 0 | 0.5 | POCl3 (1.84 mmol, 1.3 eq, 172 μl) is added dropwise to DMF (1 ml) at 0° C. and the resulting solution is stirred at 0° C. during 30 minutes. Then, a solution of 6-bromo-2-methylpyrazolo[1,5-a]pyrimidine x14 (1.415 mmol, 1 eq, 300 mg) in DMF (1 ml) is added and the mixture is stirred for 30 minutes at room temperature. ... | Cc1nn2cc(Br)cnc2c1C=O | null | 59 | null |
489,361 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][O:15][C:16]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)=[CH:19][C:17]=3[CH:18]=2)=[O:11])=[CH:5][CH:4]=1.[CH:30]1([NH2:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>CN(C)C=O>[CH:30]1([NH:36][CH2:2][C:3]2[CH:8]=[CH:... | Cc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(CCl)cc2)CCO3)cc1 | NC1CCCCC1 | 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 | A solution of N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.15g) and cyclohexylamine (0.17ml) in dimethylformamide (10ml) was stirred at room temperature for 2.5 hours. The solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/methanol/trieth... | Cc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(CNC4CCCCC4)cc2)CCO3)cc1 | null | null | null |
58,459 | ord_dataset-cb9f452f8418479ab5fd99c835dbe015 | null | 1979-01-01T00:09:00 | true | [NH2:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:5]2[CH:12]=[CH:13][C:14]([C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:4]=2[N:3]=1.Cl.[C:25](=O)(O)[O-].[Na+]>CO>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]([O:11][CH3:25])=[O:10])[C:5]2[CH:12]=[CH:13][C:14]([C:16](=[O:23])[C:17]3[CH:22]=[C... | O=C([O-])O | Nc1nc2cc(C(=O)c3ccccc3)ccc2n1CCC(=O)O | null | Cl | [Na+] | 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 | 16 | A solution of 3-(2-amino-5-benzoylbenzimidazol-1-yl)-propionic acid (6.1 g.) in methanol (30 ml.) was treated with a saturated solution (30 ml.) of hydrogen chloride in methanol. The mixture was left at room temperature for 16 hours and then evaporated. The residue was dissolved in water. The solution obtained was adju... | COC(=O)CCn1c(N)nc2cc(C(=O)c3ccccc3)ccc21 | null | null | null |
4,997 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=O)[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:18]/[C:19](/[CH3:26])=[CH:20]/C(OCC)=O)C>>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10](/[C:13](/[CH3:14])=[CH:20]/[C:19](=[O:18])[CH3:26])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | CC(=O)c1ccc(C2CCCCC2)cc1 | CCOC(=O)/C=C(\C)OCC | 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 | (E)-4-(4-cyclohexyl-phenyl)-3-pentene-2-one was prepared analogous to Example 52 from 4'-cyclohexyl-acetophenone and ethyl (E)-3-ethoxy-crotonate with a yield of 55% of theory. B.p. 148°-151°C at 0.4 mm Hg; m.p. 49°-50°C (after recrystallization from methanol and petroleum ether). Characteristic signals in NMR (CDCl3):... | CC(=O)/C=C(\C)c1ccc(C2CCCCC2)cc1 | null | 55 | null |
71,061 | ord_dataset-520610070b3c4780a03b44c7fcecc28f | null | 1980-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH:14]([CH3:16])[O:13][C:12]1=[O:17].[H][H]>[Pd].O1CCCC1>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:15][CH:14]([CH3:16])[O:13][C:12]2=[O:17])=[C:2]([Cl:1])[CH:7]=1 | [H][H] | CC1CN(c2ccc([N+](=O)[O-])cc2Cl)C(=O)O1 | null | [Pd] | 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 | null | A solution of 16.5 g of 2B and 0.5 g of 10% palladium-on-carbon catalyst in 200 ml of tetrahydrofuran was treated with hydrogen in a Parr shaker, giving 3-(4-amino-2-chlorophenyl)-5-methyl-2-oxazolidinone (2C), as a white solid, mp: 140°-141° C. | CC1CN(c2ccc(N)cc2Cl)C(=O)O1 | null | null | null |
242,916 | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | null | 1992-01-01T00:03:00 | true | I[C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([OH:13])[CH2:10][C:11]#[CH:12].Cl>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[OH:13][CH2:9][CH2:10][C:11]#[C:12][C:2]1[CH:7]=[CH:6][C:5]([C:12]#[C:11][CH2:10][CH2:9][OH:13])=[CH:4][CH:3]=1 | Ic1ccc(I)cc1 | C#CCCO | null | Cl[Pd]Cl | Cl | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 25 | 3 | First, 16.5 g of p-diiodobenzene and 8.0 g of 3-butyn-1-ol were dissolved in 200 ml of triethylamine, 0.35 g of bis(triphenylphosphine)palladium (II) chloride and 0.19 g of cuprous iodide were added thereto, and the reaction mixture was stirred under nitrogen gas flow at a room temperature for 3 hours. After the reacti... | OCCC#Cc1ccc(C#CCCO)cc1 | null | 95.2 | null |
637,707 | ord_dataset-a192df1b44174b5886ef2005f759d553 | null | 2004-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11]([O:17]CC1C=CC=CC=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]... | CCOC(=O)c1c(OC)c2cc(OCc3ccccc3)ccc2n1Cc1ccc(Cl)c(Cl)c1 | null | null | [Pd] | 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 | 12 | 5% Pd/C (100 mg) was added to a stirred solution of ethyl-N-(3,4-dichlorobenzyl)3-methoxy-5-benzyloxyindole-2-carboxylate (0.9 g) in ethyl acetate (50 ml) and the mixture was hydrogenated for 12 hours. Catalyst filtered off and filtrate evaporated to give a brown oil (0.61 g) which was used without further purification... | CCOC(=O)c1c(OC)c2cc(O)ccc2n1Cc1ccc(Cl)c(Cl)c1 | null | 83.3 | null |
1,428,555 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[O:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1>>[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:... | CC(C)c1cc(C(=O)O)oc1C(C)C | COC(=O)CCc1ccc(N)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 the same manner as that of Example 2, 4,5-diisopropylfuran-2-carboxylic acid (90 mg, 0.459 mmol) was condensed with methyl 3-[4-aminophenyl]propionate, and the resultant was purified by silica gel chromatography [benzene-ethyl acetate (14:1)] to obtain methyl 3-[4-[(4,5-diisopropylfuran-2-carbonyl)amino]phenyl]propi... | COC(=O)CCc1ccc(NC(=O)c2cc(C(C)C)c(C(C)C)o2)cc1 | null | 84 | null |
183,884 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | C([Si](CC)(CC)O[C:5]1([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:9][C:8](=O)[CH:7]=[CH:6]1)C.Cl.[NH2:21]CC(OCC)=O.C(=O)(O)[O-].[Na+].C(O)C>O>[F:13][C:12]([F:15])([F:14])[C:5]1[CH:10]=[CH:9][C:8]([NH2:21])=[CH:7][CH:6]=1 | CC[Si](CC)(CC)OC1(C(F)(F)F)C=CC(=O)C=C1 | CCOC(=O)CN | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 400 mg (1.4 mmol) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one, 572 mg (4.2 mmol) of ethyl glycinate hydrochloride, 298 mg (3.6 mmol) of sodium bicarbonate, and 10 mL of 95% ethanol was heated to reflux for 6 hours, allowed to cool to room temperature, and poured into 25 mL of water. The r... | Nc1ccc(C(F)(F)F)cc1 | null | 70.9 | null |
1,433,245 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:4]([CH3:13])[CH:3]=1.[Cu](C#N)[C:15]#[N:16]>CN1CCCC1=O.O1CCCC1>[C:15]([C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:4]([CH3:13])[CH:3]=1)#[N:16] | N#C[Cu]C#N | Cc1cc(S(N)(=O)=O)c(C)cc1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 200 | null | To a solution of 4-bromo-2,5-dimethylbenzenesulfonamide (4.6 g, 22 mmol, the product of Step A) in N-methylpyrrolidinone (30 mL) was added copper cyanide (2.5 g, 28 mmol), and the reaction mixture was heated at 200° C. for 30 min. The reaction was then allowed to cool and poured into 200 mL of crushed ice to precipitat... | Cc1cc(S(N)(=O)=O)c(C)cc1C#N | null | null | null |
1,743,423 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | C([O:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34]CC4C=CC=CC=4)=[C:27]([C:42]([F:45])([F:44])[F:43])[CH:26]=3)=[O:23])=[C:17]([F:46])[CH:16]=2)=[C:11]([O:47][CH2:48][CH3:49])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:48]([O:47][C:11]1[C... | CCOc1cc(OCc2ccccc2)ncc1-c1ccc(CC(=O)Nc2ccc(OCCOCc3ccccc3)c(C(F)(F)F)c2)c(F)c1 | null | 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 | 16 | A mixture of 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-2-fluorophenyl)-N-(4-(2-(benzyloxy)ethoxy)-3-(trifluoromethyl)phenyl)acetamide (60 mg, 0.089 mmol), Pd/C (9.46 mg, 0.089 mmol) in MeOH (10 mL) was stirred for 16 h under a H2 atmosphere at 25° C. Then the mixture was filtered and the filtrate was concentrated to gi... | CCOc1cc(=O)[nH]cc1-c1ccc(CC(=O)Nc2ccc(OCCO)c(C(F)(F)F)c2)c(F)c1 | null | 38.2 | null |
868,067 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [CH:1](O)=O.Cl.[Cl:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][Cl:11]>C=O>[ClH:5].[Cl:5][CH2:6][CH2:7][N:8]([CH3:1])[CH2:9][CH2:10][Cl:11] | ClCCNCCCl | O=CO | null | C=O | 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 | 25 | null | Formic acid (10.0 g; 0.2 mol) and 37% formaldehyde (20 ml) were mixed in a 250 ml round-bottom flask equipped with reflux condenser. 1,5-Dichloro-3-azapentane, hydrochloride (17.0 g; 0.1 mol) was added and the solution was heated with magnetic stirring at 100 C. After 3 h the temperature was increased to 120 C for 20 m... | CN(CCCl)CCCl | null | null | null |
929,423 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=[O:20].[CH2:23]([N:30]1[C:38]2[C:33](=[N:34][CH:35]=[CH:36][C:37]=2[N:39]2[CH2:48][CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40]2)[C:32]([CH3:49])=[C:31]1[CH3:50])[C:24]1[CH:29]=[CH:28][CH:27]=[CH... | Cc1c(C)n(Cc2ccccc2)c2c(N3CCc4ccccc4C3)ccnc12 | O=[N+]([O-])[O-] | null | [Ce+4] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 55 | 4 | The compound prepared in Example 6 (501.1 mg, 1.23 mmol) was treated with a saturated sodium bicarbonate solution to obtain 1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (433.6 mg, 1.18 mmol). Ammonium cerium (IV) nitrate (1.94 g, 3.54 mmol) was added at room temperature to a so... | Cc1c(CO)c2nccc(N3CCc4ccccc4C3)c2n1Cc1ccccc1 | null | null | null |
1,142,238 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [NH2:1][C:2]1[C:7]2=[C:8]([C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:47])[NH:35][C:36]4[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=4[F:46])=[C:29]([F:48])[CH:28]=3)[C:9]([CH2:24][O:25][CH3:26])=[C:10]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(... | COCc1c(-c2ccc(NC(=O)Nc3cc(C(F)(F)F)ccc3F)c(F)c2)c2c(N)ncnn2c1C1CCN(C(=O)OC(C)(C)C)CC1 | 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 | 17 | To a flask charged with tert-butyl 4-{4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl}piperidine-1-carboxylate was added methylene chloride (12.5 mL). To this suspension was added 12.5 mL of trifluoroacetic acid. The homogeneous solu... | COCc1c(-c2ccc(NC(=O)Nc3cc(C(F)(F)F)ccc3F)c(F)c2)c2c(N)ncnn2c1C1CCNCC1 | null | 70.4 | null |
819,557 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][CH:14](P(OCC)(OCC)=O)[C:15]([O:17][CH3:18])=[O:16])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:27]([C:29]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:32]=[CH:31][C:30]=1[NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=O>C1COCC1>[CH2:3]... | CC(C)(C)OC(=O)Nc1cnc(-c2ccccc2)cc1C=O | CCOP(=O)(OCC)C(NC(=O)OCc1ccccc1)C(=O)OC | 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 | 0 | 0.33 | To a slurry of 60% of sodium hydride (228 mg, 5.7 mmol) in THF (17 mL) at 0° C. was added 1A (1.88 g, 5.24 mmol) in several portions over 10 min. The reaction mixture was then brought to RT for 20 min, then cooled again at 0° C. A suspension of 3C (1.42 g, 4.76 mmol) in THF (17 mL) was added over 10 min at 0C, then the... | COC(=O)/C(=C/c1cc(-c2ccccc2)ncc1NC(=O)OC(C)(C)C)NC(=O)OCc1ccccc1 | null | 41.7 | null |
908,869 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([CH3:15])[CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([CH3:15])[CH:3]=1 | Cc1cc(Br)ccc1C(=O)CCC(=O)O | null | null | CC[SiH](CC)CC | 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 | 90 | null | To a solution of 55A (542 mg, 2 mmol) in TFA (5 mL) was added triethylsilane (0.8 mL, 5 mmol) and the mixture heated at 90° C. for 7 h. The reaction was quenched with 1N NaOH (20 mL) and washed with EtOAc (20 mL). Aqueous layer was acidified to pH 1 with 1N HCl and extracted with EtOAc (2×20 mL). The combined organics ... | Cc1cc(Br)ccc1CCCC(=O)O | null | 42 | null |
137,024 | ord_dataset-a1d4c9f5edd844798727d514977ca73e | null | 1985-01-01T00:11:00 | true | [CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[N:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:4]1)[CH3:2].CO[CH:20]1[CH2:24][CH2:23][CH:22](OC)O1>C(O)(=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:13]3[CH:20]=[CH:24][CH:23]=[CH:22]3)[N:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:... | COC1CCC(OC)O1 | CCn1cc(C(=O)O)c(=O)c2ccc(N)nc21 | null | null | null | 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 | 8 | 4.6 Grams of 1-ethyl-1,4-dihydro-4-oxo-7-amino-1,8-naphthyridine-3-carboxylic acid (U.S. Pat. No. 3,149,104) and 2.7 grams of 2,5-dimethoxytetrahydrofuran are placed under reflux for 30 minutes in 70 ml of glacial acetic acid. The mixture is allowed to cool then left for 8 hours at 5° C., and a precipitate is obtained ... | CCn1cc(C(=O)O)c(=O)c2ccc(-n3cccc3)nc21 | null | null | null |
550,550 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [CH:1]1([CH:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].Cl>C(O)C.CC(OC)(C)C>[CH:1]1([CH:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1 | CC(CCCC=O)C1CCCC1 | null | null | Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | COC(C)(C)C | null | null | null | null | null | null | null | null | null | 25 | 2 | 5-Cyclopentylhexanal (4.2 g; 25 mmol) in ethanol (40 ml) was added to sodium borohydride (1.2 g; 32 mmol) suspended in the same solvent (50 ml) at 10° C. The reaction mixture was stirred at room temperature for 2 hours and then 1 N HCl (50 ml) was added dropwise at 0° C. The mixture was diluted with MTBE (150 ml), the ... | CC(CCCCO)C1CCCC1 | null | 79.9 | null |
950,488 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:18]=2)[N:13]=[CH:12]1.[NH2:29][C:30]1[CH:34]=[CH:33][O:32][N:31]=1>>[O:32]1[CH:33]=[CH:34][C:30]([NH:29][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C... | Cc1ccc(C(=O)O)cc1-n1cnc2ccc(CN3CCOCC3)cc2c1=O | Nc1ccon1 | 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 paragraph (A) in the portion of Example 4, 4-methyl-3-[6-(morpholin-4-ylmethyl)-4-oxoquinazolin-3(4H)-yl]benzoic acid was reacted with 3-aminoisoxazole to give N-isoxazol-3-yl-4-methyl-3-[6-(morpholin-4-ylmethyl)-4-oxoquinazolin-3(4H)-yl]benzamide; NMR Spectrum: (DMSOd6) 2... | Cc1ccc(C(=O)Nc2ccon2)cc1-n1cnc2ccc(CN3CCOCC3)cc2c1=O | null | null | null |
1,363,817 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([C:22]3[CH2:27][CH2:26][C:25](=[O:28])[NH:24][N:23]=3)=[CH:17][C:16]=2[F:29])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:21][C:20]1[CH:19]=[C:18]([C:22]2[CH2:27][CH2:26][C:25](=[O:28])[NH:24][N:23]=2)[CH:17]=[C:16]([F:29])[C:15]=1[O:... | CC(C)(C)OC(=O)N1CCC(Oc2c(F)cc(C3=NNC(=O)CC3)cc2F)CC1 | 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 | 3 | A solution of 4-[2,6-difluoro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (0.42 g, 1 mmol) in methylene chloride (5 mL) was treated with trifluoro acetic acid (10 mL). The mixture was stirred at RT for 3 h and TFA was concentrated at reduced pressure to give 6-[3,5... | O=C1CCC(c2cc(F)c(OC3CCNCC3)c(F)c2)=NN1 | null | 113.2 | null |
243,823 | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | null | 1992-01-01T00:03:00 | true | C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.CCCCCC.C([Li])CCC.[CH3:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)=O.[Cl-].[Na+]>O1CCCC1>[O:31]([C:28]1[CH:27]=[CH:26][C:25]([C:23](=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)[CH3:22])=[CH:30][CH:29]=1)[C:... | CC(=O)c1ccc(Oc2ccccc2)cc1 | C[Si](C)(C)C1SCCCS1 | null | [Cl-] | [Li]CCCC | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.5 | 2-Trimethylsilyl-1,3-dithiane, 1.92 g, was dissolved in 20 ml of tetrahydrofuran and 6.3 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added to the solution in an argon flow under ice cooling. The mixture was stirred at the same temperature for 30 minutes. Then, a solution of 2.33 g of 4-phenoxyacetoph... | CC(=C1SCCCS1)c1ccc(Oc2ccccc2)cc1 | null | 85.9 | null |
537,514 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | FC(F)(F)C([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=1)=O>CC(=O)OCC>[NH2:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:16]=[CH:17][CH:18... | COC(=O)c1ccc(-c2c(NC(=O)C(F)(F)F)nc3ccc(C(=O)c4ccccc4)cn23)cc1 | null | null | null | 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 | The 2-trifluoroacetamido-3-(4-carbomethoxyphenyl)-6-benzoyl-imidazo[1,2-a]pyridine (2.13 g, 16.8 mmol) was converted to product in a manner substantially analogous to Example 67 to yield 1.44 g. (85%). EA, MS(FD). | COC(=O)c1ccc(-c2c(N)nc3ccc(C(=O)c4ccccc4)cn23)cc1 | null | null | null |
126,049 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10]3[N:18]=[CH:19][CH:20]=[CH:21][C:9]=3[N:8]=2)[CH:2]=1.[H-].[Na+].[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28]Cl>>[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28][N:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:7]([... | CN(C)CCCCl | c1cncc(C2=Nc3cccnc3Nc3ccccc32)c1 | null | [H-] | [Na+] | 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 procedure of Example 23, 6-(3-pyridinyl)-11H-pyrido[2,3-b][1,4]benzodiazepine is reacted with sodium hydride followed by reaction with 3-dimethylaminopropyl chloride to give the title compound. | CN(C)CCCN1c2ccccc2C(c2cccnc2)=Nc2cccnc21 | null | null | null |
356,556 | ord_dataset-930bf31b476c482e8ba87824089eb600 | null | 1997-01-01T00:02:00 | true | [OH:1][C:2]1[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:16]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C1C=CN=CC=1.ClCCl>[CH:16]1([C:23]([O:1][C:2]2[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[... | CCC(=O)c1cccc(C(=O)OC)c1O | O=C(Cl)C1CCCCCC1 | null | CN(C)c1ccncc1 | null | 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 | 5 | A mixture, of 7.3 g of methyl 2-hydroxy-3-propionylbenzoate, 4.7 g of 4-dimethylaminopyridine and 50 ml of dichloromethane was stirred at room temperature. Cycloheptanecarbonyl chloride, 56 g, in 10 ml of dichloromethane, (prepared as described in P. W. Collins et al., J. Med. Chem. 32, 1001-1006 (1989)) was added to t... | CCC(=O)c1cccc(C(=O)OC)c1OC(=O)C1CCCCCC1 | null | null | null |
1,565,301 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Br.[NH2:2][C:3]1[C:4]([Br:13])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[N:6]2.[C:14](Cl)(Cl)=[S:15]>O>[Br:13][C:4]1[C:3]([N:2]=[C:14]=[S:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[N:6]=[CH:7][CH:8]=[N:9]2 | S=C(Cl)Cl | Nc1ccc2nccnc2c1Br | null | Br | 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 | 25 | 2 | To a stirred solution of 6-amino-5-bromoquinoxaline hydrobromide (10 g) in distilled water (150 ml) is added thiophosgene (3 ml). The solution is stirred for two hours at room temperature and the resultant precipitate is collected by filtration, washed with water, and dried to afford 5-bromo-6-isothiocyanato-quinoxalin... | S=C=Nc1ccc2nccnc2c1Br | null | null | null |
1,548,323 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:11]([Br:12])=[CH:10][N:9]=[C:8]([Cl:13])[N:7]=2)[CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[C:47](O)=[O:48]>C(Cl)Cl>[NH:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[C:47]([N:2]1[CH... | O=C(O)c1nc2ccccc2[nH]1 | Clc1ncc(Br)c(C2CNC2)n1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | 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 | 12 | To a solution of 4-azetidin-3-yl-5-bromo-2-chloro-pyrimidine hydrochloride (0.57 mg, 2.0 mmol) in DCM (20 mL) were added HATU (1.5 g, 4.0 mmol), TEA (404 mg, 4 mmol) and 1H-benzoimidazole-2-carboxylic acid (398 mg, 2.4 mmol). The reaction mixture was stirred at RT for 12 h. TLC showed that most of starting materials we... | O=C(c1nc2ccccc2[nH]1)N1CC(c2nc(Cl)ncc2Br)C1 | null | 26.5 | null |
537,935 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [N+](=[CH2:3])=[N-].[CH3:4][C:5]([CH3:12])=[CH:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]>CCOCC>[CH3:4][C:5]([CH3:12])=[CH:6][CH2:7][CH2:8][C:9]([O:11][CH3:3])=[O:10] | CC(C)=CCCC(=O)O | C=[N+]=[N-] | 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 | 0 | null | Freshly prepared diazomethane in ether was added to an ice-cooled solution of 5-methyl-4-hexenoic acid (4.5 g, 35.16 mmol) in ether (10 mL) until the solution became slightly yellow in color. The solvent was then evaporated under vacuum to afford the title product as a colorless liquid in near quantitative yield (4.90 ... | COC(=O)CCC=C(C)C | null | null | null |
1,668,506 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH:1](/B(O)O)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1CCOCC1.Br[C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>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)... | CC(C)(C)OC(=O)c1ccc(Br)cc1 | OB(O)/C=C/c1ccccc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | 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 | 90 | 18 | To a solution of (E)-styrylboronic acid (289 mg, 1.95 mmol) in mixed solution of dioxane and water (4:1, 15 mL) were added tert-butyl 4-bromobenzoate (500 mg, 1.95 mmol), tetrakis(triphenylphosphine)palladium (225 mg, 0.2 mmol) and sodium carbonate (622 mg, 5.9 mmol). The mixture was stirred at 90° C. under nitrogen at... | CC(C)(C)OC(=O)c1ccc(/C=C/c2ccccc2)cc1 | null | 18.3 | null |
467,710 | ord_dataset-8cd3720738054d76b936f66e14d8cba6 | null | 2000-01-01T00:06:00 | true | [CH2:1]([O:8][C:9]1[C:17]2[N:13]3[C:14]([C:26]([C:30]4[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[CH:32][CH:31]=4)=[C:27]([CH2:28][CH3:29])[C:12]3=[CH:11][CH:10]=1)=[C:15]([C:22]([O:24]C)=[O:23])[C:16]=2[C:18]([O:20]C)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O... | CCc1c(-c2ccc(OCc3ccccc3)cc2)c2c(C(=O)OC)c(C(=O)OC)c3c(OCc4ccccc4)ccc1n32 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | null | Dimethyl 7-Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate (1.0 g, 1.7 mmol) was dissolved in 100 ml of methanol. Potassium hydroxide (3.37 g, 60 mmol) and 2 ml of water was added and the mixture was heated to reflux for 4 days. The reaction mixture was allowed to cool to room tempe... | CCc1c(-c2ccc(OCc3ccccc3)cc2)c2c(C(=O)O)c(C(=O)O)c3c(OCc4ccccc4)ccc1n32 | null | null | null |
1,639,938 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:10]1[CH:11]=[C:12]([NH:31][C:32]([NH:34][C@@H:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C@H:38]([O:45][C:46]3[CH:47]=[CH:48][C:49]4[N:50]([C:52]([N:55]5[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]5)=[N:53][N:54]=4)[CH:51]=3)[CH2:37][CH2:36]2)=[O:33])[N:13]([C:15]2[CH:20]=[C... | CC(C)(C)c1cc(NC(=O)N[C@H]2CC[C@@H](Oc3ccc4nnc(N5CCCCC5)n4c3)c3ccccc32)n(-c2cccc(OCCOC3CCCCO3)c2)n1 | CS(=O)(=O)Cl | 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 | 0 | null | Methane sulfonylchloride (46.0 μL, 0.59 mmol) was added to an ice cold solution of Example 39 (187 mg, 0.28 mmol) and DIPEA (122 μl, 0.70 mmol) in DCM (3.0 mL). After 2.5 h the reaction was partitioned between DCM and water. The aqueous layer was then extracted with DCM (3×). The combined organic layers were washed wit... | CC(C)(C)c1cc(NC(=O)N[C@H]2CC[C@@H](Oc3ccc4nnc(N5CCCCC5)n4c3)c3ccccc32)n(-c2cccc(OCCOS(C)(=O)=O)c2)n1 | null | 100 | null |
1,480,390 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:32]=[CH:31][C:20]2[N:21]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:22]([CH3:24])=[N:23][C:19]=2[CH:18]=1)=O)(C)(C)C>Cl>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:32]=[CH:31][C:20]2[N:21]([CH:2... | Cc1nc2cc(-c3cc4ccccc4n3C(=O)OC(C)(C)C)ccc2n1C1CCOCC1 | null | 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 | 25 | 3 | 5-(N-t-butoxycarbonylindol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole (see Synthesis Example 37 (200 mg, 0.463 mmol) was added to a 1N aqueous hydrochloric acid solution (10 mL), and this was stirred at room temperature for 3 hours. After the reaction was complete, this was allowed to stand for 3 days and the... | Cc1nc2cc(-c3cc4ccccc4[nH]3)ccc2n1C1CCOCC1 | null | null | null |
1,222,788 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [N:1]([CH2:4][C:5]1[C:6]([F:22])=[C:7]([O:12][C:13]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([Cl:21])[N:14]=2)[C:8]([Cl:11])=[CH:9][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[C:6]([F:22])=[C:7]([O:12][C:13]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([Cl:21])[N:14]=2)[C... | N#Cc1cc(Cl)nc(Oc2c(Cl)ccc(CN=[N+]=[N-])c2F)c1 | null | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 2-{[3-(azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (0.402 g, 1.189 mmol) dissolved in THF (10 mL) was treated successively with triphenylphosphine (0.468 g, 1.783 mmol) and water (0.107 mL, 5.94 mmol) at 25° C. for 16 h with stirring. The reaction mixture was concentrated to dryness and pu... | N#Cc1cc(Cl)nc(Oc2c(Cl)ccc(CN)c2F)c1 | null | 43.4 | null |
992,622 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [NH:1]([C:3](=[O:23])[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]2)=[N:11][CH:12]=1)=[O:5])[NH2:2].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([N:38]=[C:39]=S)=[CH:34][CH:33]=2)=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:30]=[CH:... | S=C=Nc1ccc(Oc2ccc(Cl)cc2)cc1 | COC(=O)C1CCN(c2ccc(NC(=O)C(=O)NN)cn2)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 | Prepared using the procedures described above for Example 631 except starting from methyl 1-(5-{[hydrazino(oxo)acetyl]amino}pyridin-2-yl)piperidine-4-carboxylate (Intermediate 83) and 1-chloro-4-(4-isothiocyanatophenoxy)benzene. 1H NMR δ 1.51-1.61 (m, 2H), 1.86-1.91 (m, 2H), 2.59-2.66 (m, 1H), 2.91-2.98 (m, 2H), 3.63 (... | COC(=O)C1CCN(c2ccc(NC(=O)c3nnc(Nc4ccc(Oc5ccc(Cl)cc5)cc4)o3)cn2)CC1 | null | null | null |
1,272,887 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[CH2:11]([P:18]([O:22][CH3:23])(=[O:21])[O:19][CH3:20])[P:12]([O:16][CH3:17])(=[O:15])[O:13][CH3:14]>>[CH3:10][O:9][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH:11]([P:12]([O:13][CH3:14])(=[O:15])[O:16][CH3:17])[P:18]([O:22][CH3:23])(=[O:21])[O:19][CH3:20])... | COP(=O)(CP(=O)(OC)OC)OC | COC(=O)CCCCCCl | 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 Synthetic Procedure B, methyl 6-chlorohexanoate is reacted with tetramethyl methanebisphosphonate to produce tetramethyl 5-methoxycarbonylpentyl-methanebisphosphonate that is then hydrolyzed to yield 5-carboxypentyl-methanebisphosphonic acid, and then hydrogenated to reduce the carboxy group to a ... | COC(=O)CCCCCC(P(=O)(OC)OC)P(=O)(OC)OC | null | null | null |
1,612,953 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH2:17]([O:19][C:20]([N:22]1[CH2:27][CH2:26][C:25]2[N:28]=[C:29]([CH2:31][OH:32])[O:30][C:24]=2[CH2:23]1)=[O:21])[CH3:18].[C:33]1(O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:17]([O:19][C:20]([N:22]1[CH2:27][CH2:26][C:25]2[N:28]=[C:29](... | CCOC(=O)N1CCc2nc(CO)oc2C1 | Oc1ccccc1 | null | CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 0.33 | Di-tert-butyl azodicarboxylate (2.20 g, 9.5 mmol) was added portionwise to a stirred solution of 6,7-dihydro-2-(hydroxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.80 g, 7.95 mmol), phenol (0.90 g, 9.5 mmol) and triphenylphosphine (2.5 g, 9.5 mmol) in THF (40 mL) at 0° C. The mixture was stirred ... | CCOC(=O)N1CCc2nc(COc3ccccc3)oc2C1 | null | 114.4 | null |
545,407 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | FC1C(O[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[C:14]3=[N:21][NH:22][C:23]2[CH:28]=[CH:27][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:25][CH:24]=2)=[O:10])=C(F)C(F)=C(F)C=1F.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH2:43][NH2:44])[CH:38]=1>>[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH2:43][... | NCc1cccnc1 | NS(=O)(=O)c1ccc(NN=C2C(=O)Nc3ccc(C(=O)Oc4c(F)c(F)c(F)c(F)c4F)cc32)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 | The title compound was prepared from 2-oxo-3[(4-sulfamoyl-phenyl)-hydrazono]-2,3-dihydro-1H-indole-5-carboxylic acid pentafluorophenyl ester and (3-pyridyl)methylamine according to Procedure K: mp 211-215° C.; Anal. Calcd for C21H18N6O4S.H2O: C, 53.84; H, 4.30; N, 17.94. Found: C, 54.29; H, 4.03; N, 17.82. | NS(=O)(=O)c1ccc(NN=C2C(=O)Nc3ccc(C(=O)NCc4cccnc4)cc32)cc1 | null | null | null |
804,443 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19](O)([CH3:20])[C:18]3[C:13](=[C:14]([N+:22]([O-])=O)[CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:22][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12](=[O:25])[N:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[C... | CC(C)(C)c1ccc(N2C(=O)c3c([N+](=O)[O-])cccc3C2(C)O)cc1 | null | 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 | 19 | The mixture of 2-(4-tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one (170 mg, Step F) and Pd/C (10 wt %, 35 mg) in 10 mL of MeOH was placed under H2 and stirred at RT for 19 h. The mixture was filtered through Celite®, condensed, and the titled compound was obtained as a colorless oil after flas... | CC1c2cccc(N)c2C(=O)N1c1ccc(C(C)(C)C)cc1 | null | null | null |
898,545 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([O:20][CH3:21])[N:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:26][... | Clc1cccc(CBr)c1 | COc1cc(C2C(=O)Nc3cc(Cl)ccc32)nc(OC)n1 | null | O=C([O-])[O-] | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC(C)=O | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of rac-6-chloro-3-(2,6-dimethoxy-pyrimidin-4-yl)-1,3-dihydro-indol-2-one (0.23 g, 0.75 mmol) (from Example 29a supra), 3-chlorobenzyl bromide (0.19 g, 0.9 mmol) (Aldrich), potassium iodide (0.15 g, 0.9 mmol) and potassium carbonate (0.23 g, 1.66 mmol) in acetone (20 mL) was heated at 80° C. for 30 minutes. Af... | COc1cc(C2(Cc3cccc(Cl)c3)C(=O)Nc3cc(Cl)ccc32)nc(OC)n1 | null | null | null |
342,924 | ord_dataset-4c84bc8a34e1469aa1b156355c91cdcc | null | 1996-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@H:20]([S:33][CH2:34][C:35]([CH3:41])([CH3:40])[CH2:36][C:37]([OH:39])=[O:38])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([OH:32])([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH-].[... | CC(C)(CS[C@H](CCc1ccccc1C(C)(C)O)c1cccc(C=Cc2ccc3ccc(Cl)cc3n2)c1)CC(=O)O | 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 the acid of Step 11 in ethanol was added 1.0 equiv of 1N NaOH. The solvent was evaporated and the remaining oil was dissolved in water and freeze-dried to yield the title compound. | CC(C)(CS[C@H](CCc1ccccc1C(C)(C)O)c1cccc(C=Cc2ccc3ccc(Cl)cc3n2)c1)CC(=O)[O-] | null | null | null |
1,003,223 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [C:1]([NH:8][C@@H:9]([C:14]([OH:16])=O)[C:10]([CH3:13])([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:38][C:39]1[N:43]2[C:44](=[O:55])[N:45]([CH2:47][CH2:48][CH:49]3[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3)[CH2:46][C:42]2=[CH:41][N:40]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3... | CC(C)(C)OC(=O)N[C@@H](C(=O)O)C(C)(C)C | Cc1ncc2n1C(=O)N(CCC1CCNCC1)C2 | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | To a solution of Boc-D-tert-leucine (0.69 g) in methylene chloride (15 ml) were added HOBt (0.61 g), WSC (0.86 g) and triethylamine (0.84 ml) under ice-cooling. The reaction mixture was mixed at 0° C. for 2.5 hours. Then, 5-methyl-2-(2-(4-piperidinyl)ethyl)-1,2-dihydroimidazo[1,5-c]imidazol-3-one (0.74 g) obtained in E... | Cc1ncc2n1C(=O)N(CCC1CCN(C(=O)[C@H](NC(=O)OC(C)(C)C)C(C)(C)C)CC1)C2 | null | 69.1 | null |
1,298,864 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [F:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][OH:10]>ClCCl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[O:10] | OCc1cccc(I)c1F | null | null | [Mn+4] | [O-2] | 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 | 50 | 3 | Manganese (IV) oxide (15.40 g, 177 mmol) was added portionwise to a stirred solution of (2-fluoro-3-iodophenyl)methanol (preparation 22c, 4.03 g, 16 mmol) in dichloromethane (140 mL) and the mixture was stirred at 50° C. After 3 hours, the mixture was filtered through Celite® and the solvent was evaporated to give the ... | O=Cc1cccc(I)c1F | null | 52.5 | null |
652,618 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][S:14][C:13]([CH3:18])([CH3:17])[C@@H:12]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:26](O)[C:27]#[C:28][CH2:29][OH:30]>>[OH:30][CH2:29][C:28]#[C:27][CH2:26][O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][C... | CC(C)(C)OC(=O)[C@@H]1N(S(=O)(=O)c2ccc(O)cc2)CCSC1(C)C | OCC#CCO | 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 | According to the procedure of Step 2 of Example 248, Mitsunobu coupling of 2.5 g (6.46 mmoL) of tert-butyl (3S)-4-[(4-hydroxyphenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxylate and 0.667 g (7.752 mmol) of 2-butyne-1,4-diol gave 1.42 g of tert-butyl (3S)-4-({4-[(4-hydroxy-2-butynyl)oxy]phenyl}sulfonyl)-2,2-dimethy... | CC(C)(C)OC(=O)[C@@H]1N(S(=O)(=O)c2ccc(OCC#CCO)cc2)CCSC1(C)C | null | 48.3 | null |
229,064 | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | null | 1991-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([C:24](OCC)=[O:25])[C:19](OCC)=[O:20].C(OCC)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:25][C:24]1[C:6]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[NH:9][C:19](=[O:20])[C:18]=1[C:13]1[CH:14]=[CH:15][... | COc1cccc(N)c1 | CCOC(=O)C(C(=O)OCC)c1ccccc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc(Oc2ccccc2)cc1 | CCOCC | null | null | null | null | null | null | null | null | null | 280 | null | A mixture of 2.7 g of m-anisidine and 5.32 g of diethyl 2-methoxyphenylmalonate in 20 ml of diphenyl ether was placed in a flask equipped with an air condenser, and heated at 270-290° C. for 2.5 hours. After cooling, to the reaction mixture there was added 80 ml of diethyl ether. The precipitates were collected by filt... | COc1ccc2c(O)c(-c3ccccc3OC)c(=O)[nH]c2c1 | null | 90.7 | null |
495,013 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([C@@:1]2([N:9]3[CH:17]=[C:... | Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | O=C(Cl)c1ccc([N+](=O)[O-])cc1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | 8 | Thymidine (2.42 g; 10 mmol) is dried by coevaporation in pyridine, then taken up in 200 ml of anhydrous pyridine and cooled to 4° C. p-Nitrobenzoyl chloride (2.04 g; 11 mmol) is added. The temperature is allowed to rise and the reaction is left overnight at room temperature. The reaction is stopped with 5 ml of saturat... | Cc1cn([C@@]2(C(=O)c3ccc([N+](=O)[O-])cc3)C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | null | 58 | null |
1,215,173 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [F:1][C:2]([F:14])([CH3:13])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([NH2:12])[CH:9]=[N:8]1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:23]2[O:27][CH:26]=[N:25][C:24]=2[C:28](O)=[O:29])[CH:20]=[CH:21][CH:22]=1>>[F:14][C:2]([F:1])([CH3:13])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([NH:12][C:28]([C:24]2[N:25]=[... | CC(F)(F)CCCCn1cc(N)cn1 | COc1cccc(-c2ocnc2C(=O)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 | Following general procedure B, starting from 1-(5,5-difluoro-hexyl)-1H-pyrazol-4-ylamine and 5-(3-methoxy-phenyl)-oxazole-4-carboxylic acid. LC-MS-conditions 05b: tR=1.12 min; [M+H]+=405.24. | COc1cccc(-c2ocnc2C(=O)Nc2cnn(CCCCC(C)(F)F)c2)c1 | null | null | null |
1,609,259 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH:1]1([N:4]2[CH2:9][C:8]3([CH2:14][CH2:13][N:12]([CH:15]([C:19]4[CH:24]=[CH:23][C:22]([C:25]5[CH:34]=[C:33]6[C:28]([CH:29]=[CH:30][CH:31]=[N:32]6)=[CH:27][CH:26]=5)=[CH:21][CH:20]=4)[C:16]([OH:18])=O)[CH2:11][CH2:10]3)[O:7][CH2:6][C:5]2=[O:35])[CH2:3][CH2:2]1.Cl.[CH3:37][N:38](C)CCCN=C=NCC.CN>ClCCl.CN(C)C1C=CN=CC=1>[... | CCN=C=NCCCN(C)C | O=C(O)C(c1ccc(-c2ccc3cccnc3c2)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2 | null | CN | CN(C)c1ccncc1 | Cl | 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 | null | 0.17 | A solution of 2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(4-(quinolin-7-yl)phenyl)acetic acid (0.191 mmol) in dichloromethane (2 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.286 mmol) and 4-(dimethylamino)pyridine (0.763 mmol) at room temperature. After stirr... | CNC(=O)C(c1ccc(-c2ccc3cccnc3c2)cc1)N1CCC2(CC1)CN(C1CC1)C(=O)CO2 | null | 26 | null |
285,704 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.B([O-])=[O:11].[Na+:13]>>[OH-:7].[Na+:13].[OH-:11].[Na+:13].[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=B[O-] | null | null | C=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Oc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A reactor equipped as in Examples A and B was charged with phenol and formaldehyde in a formaldehyde to phenol molar ratio (F/P) of about 1.5:1. The formaldehyde was charged as a 50% aqueous solution. About 3% by weight based on the total charge of sodium metaborate was added and sufficient 50% aqueous sodium hydroxide... | [OH-] | null | null | null |
1,651,616 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][O:24][CH2:25][CH3:26]>CN(C=O)C>[CH2:25]([O:24][CH2:23][O:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1)[CH3:26] | CCOCCl | CCOC(=O)c1cnc2cc(O)ccn12 | 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 | 0.5 | Ethyl 7-hydroxyimidazo[1,2-a]pyridine-3-carboxylate (100 mg, 0.38 mmol) was dissolved in DMF (3 mL) and treated with potassium carbonate (79 mg, 0.57 mmol). The mixture was stirred at ambient temperature for 30 minutes before adding chloromethylethyl ether (40 mg, 0.42 mmol) and heating mixture to 60° C. for 1 hour. Th... | CCOCOc1ccn2c(C(=O)OCC)cnc2c1 | null | 11 | null |
900,334 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)CO.O.NN.[OH-].[K+]>O>[CH2:7]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=... | O=C(c1ccccc1)c1cnc2c(C(F)(F)F)cccc2c1-c1ccccc1 | null | null | NN | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | OCCO | null | null | null | null | null | null | null | null | null | 120 | null | Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (Example 1, 0.244 g, 0.65 mmol) was taken into ethylene glycol (5 mL) along with hydrazine hydrate (0.3 mL) and heated at 120° C. for 2 hours. Next, a few pellets of KOH were added and reaction was heated at 180° C. for 4 hours. The reaction was allowed to cool... | FC(F)(F)c1cccc2c(-c3ccccc3)c(Cc3ccccc3)cnc12 | null | 54.2 | null |
934,807 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[C:5]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Cl:17])[CH:11]=1)([OH:9])[C:6]([OH:8])=[O:7].[CH2:22]1CCN2C(=NCCC2)CC1.CI>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[C:5]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Cl:17])[CH:11]=1)([OH:9])[C... | O=C(O)C(O)(c1ccc(F)c(Cl)c1)c1ccc(F)c(Cl)c1 | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | CC#N | null | null | null | null | null | null | null | null | null | null | null | 17.07 g (0.0512 mol) of 3,3′-dichloro-4,4′-difluorobenzilic acid, 14.10 g (0.0926 mol) of DBU, and 26.29 g (0.1852 mol) of methyl iodide are reacted in 200 ml acetonitrile analogously to step I.10.3. Yield: 6.77 g (38% of theory). | COC(=O)C(O)(c1ccc(F)c(Cl)c1)c1ccc(F)c(Cl)c1 | null | null | null |
1,171,426 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH2:1]([C:3]1[N:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[C:6]([I:8])[N:7]=1)[CH3:2].[F:12][C:13]1[CH:14]=[C:15]([CH2:23][CH2:24][CH:25]=O)[CH:16]=[CH:17][C:18]=1[C:19]([F:22])([F:21])[F:20]>>[CH2:1]([C:3]1[N:4]2[CH2:9][CH2:10][NH:11][CH:25]([CH2:24][CH2:23][C:15]3[CH:16]=[CH:17][C:18]([C:19]([F:20])([F:21])[F:22])=[C:13]([F... | O=CCCc1ccc(C(F)(F)F)c(F)c1 | CCc1nc(I)cn1CCN | 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 | According to the general procedure (GP10), the microwave-assisted Pictet-Spengler reaction (60 W; 100° C.; 8 bars; 10 min.) between 2-(2-ethyl-4-iodo-imidazol-1-yl)-ethylamine (312.8 mg; 1.180 mmol) and 3-(3-fluoro-4-trifluoromethyl-phenyl)-propionaldehyde (260.4 mg; 1.180 mmol) afforded 3-ethyl-8-[2-(3-fluoro-4-triflu... | CCc1nc(I)c2n1CCNC2CCc1ccc(C(F)(F)F)c(F)c1 | null | null | null |
788,331 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[I:16][C:17]1[CH:22]=[C:21]([I:23])[CH:20]=[C:19]([I:24])[C:18]=1[OH:25].[OH-].[K+]>C(O)C>[I:16][C:17]1[CH:22]=[C:21]([I:23])[CH:20]=[C:19]([I:24])[C:18]=1[O:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:... | Oc1c(I)cc(I)cc1I | O=C(O)CCCCCCCCCCCBr | null | [K+] | [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 | 12 | Ethanol (70 mL) was added with 12-bromododecanoic acid (4.8 g) and 2,4,6-triiodophenol (9.1 g) and the mixture was refluxed for dissolution. The solution was added with potassium hydroxide (2.2 g) and stirred for 12 hours. The precipitates obtained were separated by filtration, washed with ethanol and added with chloro... | O=C(O)CCCCCCCCCCCOc1c(I)cc(I)cc1I | null | 60.8 | null |
473,905 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | C[O-].[Na+].[C:4](OC(C)(C)C)(=O)C.C(O[C:15]([C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][O:23][C:20]2=[CH:21][N:22]=1)=[O:16])C.C(O)(=O)C.Cl>C1(C)C=CC=CC=1>[C:15]([C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][O:23][C:20]2=[CH:21][N:22]=1)(=[O:16])[CH3:4] | CCOC(=O)c1cc2ccoc2cn1 | CC(=O)OC(C)(C)C | null | C[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 60 | 3 | As 405 mg (7.5 mmol) of sodium methoxide was stirred in 5 mL of toluene, 1.16 g (10.0 mmol) of tert-butyl acetate was added dropwise at room temperature to the solution. Then, 956 mg (5.0 mmol) of 5-ethoxycarbonylfuro[2,3-c]pyridine dissolved in 5 mL of toluene was added dropwise at room temperature to the above soluti... | CC(=O)c1cc2ccoc2cn1 | null | 72 | null |
620,769 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [OH-].[Na+:2].C([O:5][C:6]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([O:15][CH3:16])[CH:9]=1)=[O:7])C>C1COCC1>[Na+:2].[CH3:16][O:15][C:10]1[CH:9]=[C:8]([C:6]([O-:7])=[O:5])[CH:13]=[C:12]([CH3:14])[N:11]=1 | CCOC(=O)c1cc(C)nc(OC)c1 | null | null | [Na+] | [OH-] | 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 | 0.33 | A 6.1 ml portion of 1 N aqueous sodium hydroxide was added to 10 ml of THF containing 1.20 g of 2-methoxy-6-methyl-4-pyridinecarboxylic acid ethyl ester and stirred at room temperature for 1 hour and 20 minutes, and then the reaction solvent was evaporated to obtain 2-methoxy-6-methyl-4-pyridinecarboxylic acid sodium s... | COc1cc(C(=O)[O-])cc(C)n1 | null | null | null |
1,156,992 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | B([C:4]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:5]=1[O:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])(O)O.Br[C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])=[CH:23][CH:22]=1>>[CH3:31][N:30]([CH3:32])[S:27]([C:24]1[CH:23]=[CH:22][C:21]([C:4]2[CH:15]=[C:14]([C:16]([F:19])([F... | CN(C)S(=O)(=O)c1ccc(Br)cc1 | C[C@H](Oc1ccc(C(F)(F)F)cc1B(O)O)C(=O)O | 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 by the method of example 144 step (i) using the product from example 146 step (iv) and 4-bromo-N,N-dimethyl-benzenesulfonamide. | C[C@H](Oc1ccc(C(F)(F)F)cc1-c1ccc(S(=O)(=O)N(C)C)cc1)C(=O)O | null | null | null |
1,031,353 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:11]([CH:22]([CH3:24])[CH3:23])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]Br.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[C:13]([Br:25])=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[N... | BrBr | COc1ccc(-c2cc(OCc3ccccc3)nn2C(C)C)cc1 | null | O=C([O-])O | [Na+] | 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 | null | 1 | To a solution of 3-benzyloxy-1-isopropyl-5-(4-methoxy-phenyl)-1H-pyrazole (3.7 g) in dichloromethane (50 mL) was added bromine (0.98 mL) at 0° C., and the mixture was stirred for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated. The or... | COc1ccc(-c2c(Br)c(OCc3ccccc3)nn2C(C)C)cc1 | null | null | null |
443,597 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[O:13][CH3:14].S(=O)(=O)(O)O.[CH3:20]O>>[OH:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:20])=[O:9])=[CH:4][C:3]=1[O:13][CH3:14] | CO | COc1cc(C=CC(=O)O)ccc1O | null | O=S(=O)(O)O | 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 | -25 | null | 100 g of 4-hydroxy-3-methoxycinnamic acid were dissolved in 1 l of methanol and treated with 14.4 ml of concentrated sulphuric acid. The solution was heated under reflux for 2.5 hrs. Subsequently, the majority of the methanol (about 750 ml) was distilled off and the residue remaining was poured into 1 l of water. Then,... | COC(=O)/C=C/c1ccc(O)c(OC)c1 | null | null | null |
738,323 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([CH:21]=[O:22])[C:15]=2[F:23])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([CH2:... | CCOC(C(=O)NCc1ccc(C#N)cc1)c1c(F)ccc(C=O)c1F | null | null | [BH4-] | [Na+] | 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 | 4 | A suspension of (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-formyl-phenyl)-2-ethoxy-acetamide (300 mg) in EtOH (1 ml) was treated with NaBH4 (66 mg) at 0°. The reaction mixture was stirred for 4 hrs at rt, then poured onto ice and extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtrated and con... | CCOC(C(=O)NCc1ccc(C#N)cc1)c1c(F)ccc(CO)c1F | null | 57.7 | null |
934,149 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [NH:1]1[C:5]([C:6]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH:9]=[CH:8][N:7]=2)=[N:4][N:3]=[N:2]1.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]=[C:29]=[O:30])[CH:23]=1>>[NH:4]1[C:5]([C:6]2[CH:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][C:16]([NH:19][C:29]([NH:... | O=C=Nc1cccc(C(F)(F)F)c1 | Nc1ccc(Oc2ccnc(-c3nnn[nH]3)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 | 4 | The title compound is prepared as described in Example 102 but using 4-[2-(1H-tetrazol-5-yl)-pyridin-4-yloxy]-phenylamine and α,α,α-trifluoro-m-tolyl-isocyanate. The reaction mixture is stirred for 4 h. The crude product Is washed with a solution of CH2Cl2/MeOH (95/5) and dried In vacuo to afford the title compound as ... | O=C(Nc1ccc(Oc2ccnc(-c3nnn[nH]3)c2)cc1)Nc1cccc(C(F)(F)F)c1 | null | null | null |
1,672,813 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH3:1][C@:2]([NH:24]C(=O)OC(C)(C)C)([C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[CH:12][CH:13]=1)=[O:6])[CH2:3][CH3:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:11]2[N:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C@:2]([CH3:1])([... | CC[C@@](C)(NC(=O)OC(C)(C)C)C(=O)Nc1ccc(Oc2ccc(C)c(OC)c2)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 | To a solution of 1,1-dimethylethyl ((1R)-1-methyl-1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 98, 65 mg) in dry dichloromethane (3 mL) cooled to 0° C., TFA (0.700 mL, 9.08 mmol) was added dropwise. The reaction was stirred at that temperature for 2 hours. The rea... | CC[C@](C)(N)C(=O)Nc1ccc(Oc2ccc(C)c(OC)c2)nc1 | null | 88.3 | null |
457,239 | ord_dataset-2501595af7f242268dbaab34c9e7ae56 | null | 2000-01-01T00:02:00 | true | [H-].[Na+].[CH2:3]([SH:7])[CH2:4][CH2:5][SH:6].[CH2:8]([C:15]([N:33]([CH3:35])[CH3:34])([CH2:31][CH3:32])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CN(C)C=O>[CH2:8]([C:15]([N:33]([CH3:35])[CH3:34])([CH2:... | CCC(Cc1ccccc1)(C(=O)c1ccc(-c2ccc(Br)cc2)cc1)N(C)C | SCCCS | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 100 | 2 | 9.2 mmol of sodium hydride are suspended in 40 ml of dry dimethylformamide and 2.3 ml (23 mmol) of 1,3-propanedithiol are added dropwise. Then 2.0 g (4.6 mmol) of 2-benzyl-1-(4'-bromo-biphenyl-4-yl)-2-dimethylamino-butan-1-one (prepared by the method described in U.S. Pat. No. 5,534,629) in 60 ml of dimethylformamide a... | CCC(Cc1ccccc1)(C(=O)c1ccc(-c2ccc(SCCCS)cc2)cc1)N(C)C | null | null | null |
1,598,535 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | Cl[C:2]1[N:3]=[C:4]2[S:11][C:10]([CH2:12][CH3:13])=[N:9][N:5]2[C:6](=[O:8])[CH:7]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:12]([C:10]1[S:11][C:4]2=[N:3][C:2]([N:17]3[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:2... | CCc1nn2c(=O)cc(Cl)nc2s1 | CC(C)(C)OC(=O)N1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 150 | null | To a solution of 7-chloro-2-ethyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (2.0 g, 9.27 mmol, 1.0 equiv) in 50 mL of anhydrous acetonitrile in a microwave vial is added tert-butyl 1-piperazinecarboxylate (2.073 g, 11.13 mmol, 1.2 equiv) followed by N,N-diisopropylethylamine (4.86 mL, 27.8 mmol, 3.0 equiv). The mixtu... | CCc1nn2c(=O)cc(N3CCN(C(=O)OC(C)(C)C)CC3)nc2s1 | null | null | null |
902,911 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:7](N)([NH2:10])(=[O:9])=[O:8]>O1CCOCC1>[N:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | NS(N)(=O)=O | C1CCNCC1 | null | null | 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 | Piperidine (3.0 g) and sulfamide (5.93 g) in 1,4-dioxane (100 ml) were heated at reflux for 24 h. The solvent was evaporated under reduced pressure and the resulting solid suspended in CHCl3. The suspension was filtered and the filtrate concentrated in vacuo to afford the subtitle compound as a white solid. Yield: 3.85... | NS(=O)(=O)N1CCCCC1 | null | null | null |
1,139,433 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | C[Al](C)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([NH2:22])[NH:20][N:21]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.[CH3:23][C@H:24]1[N:29]([CH3:30])[C@@H:28]([CH3:31])[CH2:27][N:26]([C:32]2[N:37]=[CH:36][C:35]([C:38](OC)=[O:39])=[CH:34][N:33]=2)[CH2:25]1.Cl>C1(C)C=CC=CC=1.CO>[CH3:14][O:13][... | COc1cc(CCc2cc(N)[nH]n2)cc(OC)c1 | COC(=O)c1cnc(N2C[C@@H](C)N(C)[C@@H](C)C2)nc1 | null | C[Al](C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CO | null | null | null | null | null | null | null | null | null | 60 | 18 | Trimethylaluminium (2M in toluene, 1.04 ml, 2.08 mmol) was added dropwise to a suspension of 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (205 mg, 0.83 mmol) and methyl 2-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)pyrimidine-5-carboxylate (220 mg, 0.83 mmol) in toluene (5.257 ml) at 25° C. The resulting solution was... | COc1cc(CCc2cc(NC(=O)c3cnc(N4C[C@@H](C)N(C)[C@@H](C)C4)nc3)[nH]n2)cc(OC)c1 | null | 39.4 | null |
207,225 | ord_dataset-dd1de64954674e17b4b690cac09dc67b | null | 1990-01-01T00:04:00 | true | [CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=O)[CH2:14][CH2:15][N:16]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH3:17])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][CH2:13][CH2:14][CH2:... | CCCCOc1ccc(NC(=O)CCN(C)CCc2ccc(OC)c(OC)c2)cc1 | null | null | [Al+3] | [H-] | [Li+] | 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 a manner similar to Preparation 2 react N-[4-butoxyphenyl]-3-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]propionamide with lithium aluminum hydride to obtain the title compound. | CCCCOc1ccc(NCCCN(C)CCc2ccc(OC)c(OC)c2)cc1 | null | null | null |
1,417,611 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | CC(=C)C[O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:8]([O:10][CH3:11])=[O:9]>ClCCl>[OH:4][C:5]1[C:6]([CH2:8][C:7]([CH3:12])=[CH2:6])=[C:7]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:8]([O:10][CH3:11])=[O:9] | C=C(C)COc1cc(C(=O)OC)ccc1[N+](=O)[O-] | null | null | null | null | 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 | 3 | Methyl 3-(2-methylallyloxy)-4-nitro-benzoate 4a (4.52 g, 18 mmol) was heated to 190° C. and stirred for 3 hours. The reaction mixture was cooled down to room temperature followed by the addition of 50 mL of dichloromethane. The reaction solution was concentrated under reduced pressure. The resulting residue was purifie... | C=C(C)Cc1c(C(=O)OC)ccc([N+](=O)[O-])c1O | null | 115 | null |
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