Trifluoroacetic acid → Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

HRID 1432951ノート

反応式

HRID 1432951 の反応式
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:24])[C:18]=2[CH:17]=[C:16]1[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:28][C:27]1=[O:42])=O)(C)(C)C>C(Cl)Cl>[CH2:35]([O:34][C:32]([N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:16]2[NH:15][C:23]3[CH:22]=[CH:21][N:20]=[C:19]([Cl:24])[C:18]=3[CH:17]=2)[C:27](=[O:42])[CH2:28]1)=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86760978HCID 86760978、化合物

生成物 1

HCID 53757606Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Trifluoroacetic acid (10 mL) is added to a solution of 2-(4-benzyloxycarbonyl-2-oxo-piperazin-1-ylmethyl)-4-chloro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (5.66 g, 11.3 mmol, prepared in the same manner as described previously) in CH2Cl2 (10 mL). The solution is stirred overnight then diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (3.81 g, 9.56 mmol) as a foamy yellow solid. 1H NMR (CDCl3, 300 MHz) δ9.43 (bs, 1H), 8.08 (d, 1H), 7.38 (s, 5H), 7.18 (d, 1H), 6.51 (s, 1H), 5.15 (s, 2H), 4.58 (s, 2H), 4.20 (s, 2H), 3.71 (m, 2H), 3.50 (m, 2H). Ion spray [M+H]+=399, 401, Cl pattern.

後処理

  1. customprepared in the same manner
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product is chromatographed
  7. washeluting with 1-5% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-89c763872df94fb49082851a202ac181
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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