1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178419노트

반응식

HRID 1178419 반응식
ON1C2C=CC=CC=2N=N1.[Cl:11][C:12]1[S:41][C:15]2[NH:16][C:17]([C:19]([NH:21][CH:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:32][C@H:33]4COC(C)(C)O4)[C:23]3=[O:40])=[O:20])=[CH:18][C:14]=2[CH:13]=1.ClC1S[C:46]2[NH:47][C:48](C(NC3CC4C(=CC=CC=4)N(CC(O)CO)C3=O)=O)=CC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:11][C:12]1[S:41][C:15]2[NH:16][C:17]([C:19]([NH:21][CH:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:32][CH2:33][N:47]([CH3:48])[CH3:46])[C:23]3=[O:40])=[O:20])=[CH:18][C:14]=2[CH:13]=1

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 103442072-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxolan-4(S)-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3(R,S)-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide

생성물 1

HCID 103646262-Chloro-N-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide수율 56%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

1-Hydroxybenzotriazole (0.69 g, 0.51 mmol) was added to a solution of 3-amino-1-[2-(dimethylamino)ethyl]-3,4-dihydroquinolin-2(1H)-one (Method 10, 100 mg, 0.427 mmol) in DMF (3 mL) followed by 2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid (Method 9, 86 mg, 0.42 mmol) and EDCI (0.98 g, 0.51 mmol). The reaction was diluted with EtOAc (40 mL) and sat. aqueous NaHCO3 (20 mL) and the separated organic layer was dried (MgSO4), filtered and evaporated to dryness. Purification by column chromatography (MeOH:DCM 1:9) afforded the title compound (70 mg, 56%) as a yellow solid.

후처리

  1. dry with materialthe separated organic layer was dried (MgSO4)
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customPurification by column chromatography (MeOH:DCM 1:9)

출처 및 근거

ORD 기록
ord-a02d7889a50d4ac3989014fab87f1eab
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276517B2

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