3-Fluorobenzenesulfonamide → N-(4-(1,4-diazepan-1-yl)-2-{[(3-fluorophenyl)sulfonyl]amino}phenyl)-3-fluorobenzenesulfonamide hydrochloride

HRID 1064472

반응식

HRID 1064472 반응식
NC1C=CC(N2CCCN(C(OC(C)(C)C)=O)CC2)=CC=1N.[F:23][C:24]1[CH:25]=[C:26]([S:30]([Cl:33])(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1.[NH2:34][C:35]1[CH:40]=[C:39]([N:41]2[CH2:47][CH2:46][CH2:45][N:44](C(OC(C)(C)C)=O)[CH2:43][CH2:42]2)[CH:38]=[CH:37][C:36]=1[NH:55][S:56]([C:59]1[CH:64]=[CH:63][CH:62]=[C:61]([F:65])[CH:60]=1)(=[O:58])=[O:57].FC1C=C(S(N)(=O)=O)C=CC=1.Cl.CCOCC>CO>[ClH:33].[N:41]1([C:39]2[CH:38]=[CH:37][C:36]([NH:55][S:56]([C:59]3[CH:64]=[CH:63][CH:62]=[C:61]([F:65])[CH:60]=3)(=[O:57])=[O:58])=[C:35]([NH:34][S:30]([C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[CH:25]=3)(=[O:32])=[O:31])[CH:40]=2)[CH2:47][CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1

참가 물질

7

반응물 5

HCID 1509243-FluorobenzenesulfonamideHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 10953452Ether hydrochlorideHCID 22272464Tert-butyl 4-(3,4-diaminophenyl)-1,4-diazepane-1-carboxylateHCID 22272531N-{2-amino-4-[4-t-butyloxycarbonyl-homopiperazin-1-yl-]phenyl}3-fluorobenzenesulfonamide

생성물 1

HCID 10209725N-(4-(1,4-diazepan-1-yl)-2-{[(3-fluorophenyl)sulfonyl]amino}phenyl)-3-fluorobenzenesulfonamide hydrochloride

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The compound was prepared from 2-amino-5-(4-t-butyloxycarbonyl-1-homopiperazinyl)aniline and 3-flourobenzenesulfonyl chloride. Purification by column chromatography (CH2Cl2/MeOH/heptane, 4:1:15) gave a mixture of N-{2-amino-4-[4-t-butyloxycarbonyl-homopiperazin-1-yl-]phenyl}3-fluorobenzenesulfonamide and N-{4-[4-t-butyloxycarbonyl]homopiperazinyl)-2-[(3-flourophenylsulfonyl)amino]phenyl}-3-fluorobenzenesulfonamide (0.180 g, 73%). Boc-deprotection was achieved by dissolving the mixture in small amount of MeOH and adding HCl/ether. The mixture was let at r.t. for 0.5 h. Purification by preparative HPLC gave N-(4-(1,4-diazepan-1-yl)-2-{[(3-fluorophenyl)sulfonyl]amino}phenyl)-3-fluorobenzenesulfonamide hydrochloride Anal. (C23H27ClN4O4S2) C, H, N, S.; M+ 524.4 Calcd 522.12.

후처리

  1. customPurification by column chromatography (CH2Cl2/MeOH/heptane, 4:1:15)
  2. customgave
  3. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-0e29388b0e1b479daf21d790faf6c9e1
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969710B2

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