Triethylamine → N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1-(tert-butoxycarbonylmethyl)indole-2-carboxamide

HRID 2257132노트

반응식

HRID 2257132 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[O:19][CH3:20])[N:6]=1.[C:21]([O:25][C:26]([CH2:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[C:38](O)=[O:39])=[O:27])([CH3:24])([CH3:23])[CH3:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl.O>[F:18][C:15]([F:16])([F:17])[C:10]1[CH:11]=[C:12]([O:13][CH3:14])[C:7]([C:5]2[N:6]=[C:2]([NH:1][C:38]([C:30]3[N:29]([CH2:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[C:37]4[C:32]([CH:31]=3)=[CH:33][CH:34]=[CH:35][CH:36]=4)=[O:39])[S:3][CH:4]=2)=[C:8]([O:19][CH3:20])[CH:9]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 190280212-Amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazoleHCID 21749024N-(tert-butoxycarbonylmethyl)-2-indolecarboxylic acid

생성물 1

HCID 19028034N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1-(tert-butoxycarbonylmethyl)indole-2-carboxamide수율 70.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 0.609 g of 2-amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazole, 0.606 g of N-(tert-butoxycarbonylmethyl)-2-indolecarboxylic acid, 1.062 g of BOP and 0.243 g of triethylamine in 30 ml of DCM is stirred at r.t. for 24 hours. 50 ml of water are then added, and the organic phase is separated after settling has taken place, dried over sodium sulphate and evaporated under vacuum. The residue is chromatographed on silica H, eluting with a DCM/AcOEt (100:5; v/v) mixture. 0.79 g of the expected product is obtained after crystallization in ether, m.p.=214°-216° C.

후처리

  1. customthe organic phase is separated after settling
  2. dry with materialdried over sodium sulphate
  3. customevaporated under vacuum
  4. customThe residue is chromatographed on silica H
  5. washeluting with a DCM/AcOEt (100:5; v/v) mixture

출처 및 근거

ORD 기록
ord-45d196adc7644d52b2b1ebfe1993d1f2
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05656648

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