Hydrazine → (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate

HRID 416353

反応式

HRID 416353 の反応式
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:42])[O:11][CH2:12][C@@H:13]([N:28]([CH3:41])[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=2[Cl:40])=[O:30])[CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)=[N:7][CH:8]=1.NN>CO>[F:44][C:2]([F:1])([F:43])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:42])[O:11][CH2:12][C@@H:13]([N:28]([CH3:41])[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=2[Cl:40])=[O:30])[CH2:14][CH2:15][CH2:16][NH2:17])=[N:7][CH:8]=1

参加物

4

反応物 2

HCID 9321HydrazineHCID 57947787(S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(1,3-dioxoisoindolin-2-yl)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate

生成物 1

HCID 57947682(S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate収率 76%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(1,3-dioxoisoindolin-2-yl)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate (150 mg, 0.24 mmol) in MeOH (5.0 mL) was added NH2NH2 (0.2 mL). The reaction mixture was stirred at RT for 2 h. The mixture was concentrated, dissolved in MeOH, filtered, and purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate (91 mg, 76%). LRMS (M+H+) m/z 506.1.

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in MeOH
  3. filtrationfiltered
  4. custompurified on RP-HPLC
  5. additiona mixture of acetonitrile and H2O

出典と根拠

ORDレコード
ord-e7d97fe9f8be4c088b699696f1acb099
出典データセット
uspto-grants-2012_01
特許番号
US08088793B2

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