(r)-Tert-butyl 1-(4-(5-carbamoyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate → (R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 79519ノート

反応式

HRID 79519 の反応式
[C:1]([C:4]1[C:5]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:37])[C@H:20]([NH:29]C(=O)OC(C)(C)C)[CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)(=O)[NH2:2]>O=P(Cl)(Cl)Cl>[NH2:29][C@H:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[C:19]([N:16]1[CH2:17][CH2:18][N:13]([C:5]2[C:4]([C:1]#[N:2])=[CH:9][N:8]=[C:7]3[NH:10][CH:11]=[CH:12][C:6]=23)[CH2:14][CH2:15]1)=[O:37]

参加物

3

反応物 1

HCID 68761929(r)-Tert-butyl 1-(4-(5-carbamoyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

生成物 1

HCID 44198751(R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile収率 7.4%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
70 °C

実験手順

(R)-tert-Butyl 1-(4-(5-carbamoyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.035 g, 0.066 mmol) was placed in POCl3 (2 mL) and heated to 70° C. for 2 hours. The reaction was then concentrated, diluted with DCM, and washed with saturated NaHCO3. The organic fraction was dried, filtered and concentrated to give a crude residue. The residue was purified (SP4, 12+M, water/CAN 95/5→60/40, 20CV) to give (R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (0.002 g, 7.4% yield). MS ESI (+) m/z 409 detected.

後処理

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with DCM
  3. washwashed with saturated NaHCO3
  4. customThe organic fraction was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude residue
  8. customThe residue was purified (SP4, 12+M, water/CAN 95/5→60/40, 20CV)

出典と根拠

ORDレコード
ord-674da9d08c5d42b79b70932db553a418
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

反応ノート

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