Benzenesulfonyl chloride → HCID 86760979、化合物

HRID 1432952ノート

反応式

HRID 1432952 の反応式
[OH-].[Na+].[C:3]1([S:9](Cl)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[NH:38][C:37]3[CH:36]=[CH:35][N:34]=[C:33]([Cl:39])[C:32]=3[CH:31]=2)[C:25](=[O:40])[CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.C(Cl)Cl>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[N:38]([S:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)(=[O:11])=[O:10])[C:37]3[CH:36]=[CH:35][N:34]=[C:33]([Cl:39])[C:32]=3[CH:31]=2)[C:25](=[O:40])[CH2:24]1)=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53757606Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

生成物 1

HCID 86760979HCID 86760979、化合物収率 98.1%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Powdered NaOH (0.96 g, 23.9 mmol) followed by nBu4NHSO4 (0.32 g, 0.96 mmol) and benzene sulfonyl chloride (1.8 mL, 14.1 mmol) is added to a solution of 4-(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (3.81 g, 9.56 mmol) in CH2Cl2(32 mL) at RT. The resulting slurry is stirred for 3.5 h 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 (5.06 g, 9.38 mmol). 1H NMR (CDCl3, 300 MHz) δ8.23 (d, 1H), 7.97 (d, 1H), 7.84 (d, 2H), 7.61 (d, 1H), 7.51 (m, 2H), 7.38 (s, 5H), 6.50 (s, 1H), 5.18 (s, 2H), 5.03 (s, 2H), 4.29 (s, 2H), 4.29 (s, 2H), 3.80 (m, 2H), 3.51 (m, 2H). Ion spray [M+H]+=539, 541, Cl pattern.

後処理

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

出典と根拠

ORDレコード
ord-5ebdf93f370b4244ac2be3ab1a28ed16
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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