Benzenesulfonyl chloride → HCID 86760979, 화합물

HRID 1432952노트

반응식

HRID 1432952 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 86760979HCID 86760979, 화합물수율 98.1%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ebdf93f370b4244ac2be3ab1a28ed16
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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