Water → tert-Butyl (1S,2R)-2-(7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

HRID 2092769ノート

反応式

HRID 2092769 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:12]3[C:13](=[O:16])[NH:14][CH2:15][C:11]=3[CH:10]=[C:9]([NH:17][C@@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[N:8]=2)[CH:4]=[N:3]1.[Cl:32]N1C(=O)CCC1=O.O.C(Cl)(Cl)Cl>C(Cl)Cl>[Cl:32][C:10]1[C:11]2[CH2:15][NH:14][C:13](=[O:16])[C:12]=2[C:7]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)=[N:8][C:9]=1[NH:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29]

参加物

6

反応物 4

HCID 962WaterHCID 6212ChloroformHCID 31398Chlorosuccinimide2 回HCID 86654709tert-Butyl (1S,2R)-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

生成物 1

HCID 86654711tert-Butyl (1S,2R)-2-(7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate収率 62%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl (1S,2R)-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (30 mg, 0.070 mmol) and N-chlorosuccinimide (9.86 mg, 0.074 mmol) in DCM (1 mL) was stirred at RT overnight. Additional N-chlorosuccinimide (1 eq) was added and the mixture was stirred at RT for 3 h. Water and CHCl3 were added to the mixture and the organic phase was washed with brine, dried over MgSO4, and evaporated. The residue was purified by preparative HPLC to give the title compound (20 mg, 61.7%). 1H NMR (500 MHz, CDCl3) δ ppm 1.18-2.09 (m, 17H), 4.02 (s, 3H), 4.28-4.45 (m, 2H), 5.80 (br s, 1H), 8.39 (br s, 1H), 9.03 (br s, 1H). [M+H] calc'd for C22H29ClN6O3, 461. found, 461.

後処理

  1. washthe organic phase was washed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-08e41c9038ae48389120bf43cb82bf9b
出典データセット
uspto-grants-2013_05
特許番号
US08440689B2

反応ノート

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