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 1178419ノート

反応式

HRID 1178419 の反応式
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

参加物

8

反応物 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

生成物 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-carboxamide収率 56%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a02d7889a50d4ac3989014fab87f1eab
出典データセット
uspto-grants-2007_10
特許番号
US07276517B2

反応ノート

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