Chlorosuccinimide → HCID 66897365, 화합물

HRID 2044130

반응식

HRID 2044130 반응식
[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:14][S:15]([C:18]1[C:19]2[CH:20]=[CH:21][NH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:17])=[O:16])[CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]#[N:13].CC(SCC[NH2+]C(CN)=O)=O.C([O-])(C(F)(F)F)=O.C1C(=O)N([Cl:53])C(=O)C1>CN(C=O)C.CC#N>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:14][S:15]([C:18]1[C:19]2[C:20]([Cl:53])=[CH:21][NH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:17])=[O:16])[CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]#[N:13]

참가 물질

6

반응물 3

HCID 31398ChlorosuccinimideHCID 57219S-acetyl-N-glycylcysteamineHCID 66897272HCID 66897272, 화합물

생성물 1

HCID 66897365HCID 66897365, 화합물수율 69.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

A solution of 0.20 g (0.52 mmol) of 4-(2-cyano-pyrrol-1-yl)-2-(1H-indole-4-sulfonylamino)-butyric acid methyl ester (from the synthesis of I-102) and 0.070 g (0.52 mmol) of NCS in 1 mL of DMF is stirred overnight, and then diluted with MeCN and purified by preparative HPLC to provide 0.15 g (0.36 mmol; 69%) of 2-(3-chloro-1H-indole-4-sulfonylamino)-4-(2-cyano-pyrrol-1-yl)-butyric acid methyl ester. This material is stirred in 1.4 mL of THF with 1.4 mL of 1M NaOH for 3 h, and then 2N HCl is added until the pH is 3. The mixture is extracted with EtOAc, and the extract washed with brine, dried over Na2SO4, filtered, and concentrated to provide 0.12 g (85%) of I-103 as a tan powder.

후처리

  1. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-96dffca45bf84fa2b227af2e5e7b47e7
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586748B2

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