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

HRID 2257132Notes

Reaction equation

HRID 2257132 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-45d196adc7644d52b2b1ebfe1993d1f2
Source dataset
uspto-grants-1997_08
Patent number
US05656648

Reaction notes

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