Indoline → Tert-butyl 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

HRID 1167808노트

반응식

HRID 1167808 반응식
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]([CH3:39])[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:26][CH:25]=2)=[O:22])=[CH:16][C:15]=1[O:40][CH3:41].[NH:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43]1>ClCCl.C(N(CC)CC)C>[N:42]1([C:5]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH:30]([CH3:39])[CH2:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])=[CH:26][CH:25]=3)=[O:22])=[CH:16][C:15]=2[O:40][CH3:41])=[O:11])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43]1

참가 물질

6

반응물 3

HCID 10328IndolineHCID 94429TriphosgeneHCID 22994176Tert-butyl 3-[4-({4-amino-3-methoxyphenyl}acetylamino)phenyl]butyrate

생성물 1

HCID 22994266Tert-butyl 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

Triphosgene (150 mg) was added to a stirred solution of tert-butyl 3-[4-({4-amino-3-methoxyphenyl}acetylamino)phenyl]butyrate (540 mg, Reference Example 2) in dichloromethane (50 ml) at 0-5° C. under an atmosphere of nitrogen. After stirring for one hour the mixture was treated with a solution of indoline (0.15 ml) in dichloromethane (2.5 ml) and triethylamine (0.51 ml). This mixture was allowed to stand at room temperature overnight and then evaporated. The residual gummy solid was suspended in water and the suspension was acidified to pH 1 by addition of hydrochloric acid. The resulting pale green solid was filtered and then subjected to flash chromatography on silica eluting with 0.2% to 1% methanol in dichloromethane to give the title compound (580 mg) as an off-white solid.

후처리

  1. waitto stand at room temperature overnight
  2. customevaporated
  3. additionthe suspension was acidified to pH 1 by addition of hydrochloric acid
  4. filtrationThe resulting pale green solid was filtered

출처 및 근거

ORD 기록
ord-4b586571773d4d0d8afe78a917fb1476
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620832B2

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