Triethylamine → (S)-4-(4-(2-(pyrrolidin-2-yl)acetyl)piperazin-1-yl)-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60266

反応式

HRID 60266 の反応式
[N:1]1([C:7]2[C:15]3[C:14]4[CH:16]=[C:17]([C:20]#[N:21])[N:18]=[CH:19][C:13]=4[N:12](COCC[Si](C)(C)C)[C:11]=3[N:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(OC([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42][C:43](O)=[O:44])=O)(C)(C)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(Cl)Cl>[NH:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42][C:43]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:15]3[C:14]4[CH:16]=[C:17]([C:20]#[N:21])[N:18]=[CH:19][C:13]=4[NH:12][C:11]=3[N:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5]1)=[O:44]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 688605(S)-2-(1-BOC-2-pyrrolidinyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672574164-(piperazin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

生成物 1

HCID 53250548(S)-4-(4-(2-(pyrrolidin-2-yl)acetyl)piperazin-1-yl)-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 4-(piperazin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (100 mg, 0.2 mmol), (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acetic acid (220 mg, 1.0 mmol), 1-hydroxybenzotriazole (50 mg, 0.4 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrogen chloride (70 mg, 0.4 mmol), and triethylamine (0.1 mL, 0.7 mmol) in methylene chloride (2.5 mL) was stirred at ambient temperature overnight. The reaction mixture was diluted with methylene chloride (50 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 0-70% ethyl acetate in heptane) to afford the title compound as a white foam, which was used in the next step without any further purification (140 mg).

後処理

  1. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified flash chromatography (silica, 4 g, ISCO, 0-70% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-b31be6760dfb40c4b15d92d1ee43ef56
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

関連ノート

読み込み中…