Sodium Carbonate → N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1H-indole-2-carboxamide

HRID 2257131Notes

Reaction equation

HRID 2257131 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([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:33](O)=[O:34])(=O)C.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(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CO.O.C(N(CC)CC)C>[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:33]([C:25]3[NH:24][C:32]4[C:27]([CH:26]=3)=[CH:28][CH:29]=[CH:30][CH:31]=4)=[O:34])[S:3][CH:4]=2)=[C:8]([O:19][CH3:20])[CH:9]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 102198671-acetylindole-2-carboxylic AcidHCID 190280212-Amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazole

Product 1

HCID 19028003N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1H-indole-2-carboxamideYield 60.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 0.609 g of 2-amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazole, 0.447 g of N-acetyl-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 48 hours. 100 ml of water are added, and the organic phase is separated after settling has taken place, dried over sodium sulphate and evaporated under vacuum. The derivative acetylated on the indole nitrogen which is obtained is taken up in 50 ml of MeOH, 2 g of sodium carbonate are added and the mixture is stirred overnight at r.t. It is evaporated under vacuum, the residue is taken up with 100 ml of water, the mixture is extracted with DCM, and the organic phase is dried over sodium sulphate and evaporated under vacuum. 0.54 g of the expected product is obtained after crystallization in DCM, m.p.>260° C.

Workup

  1. customthe organic phase is separated after settling
  2. dry with materialdried over sodium sulphate
  3. customevaporated under vacuum
  4. customis obtained
  5. stirringthe mixture is stirred overnight at r.t
  6. customIt is evaporated under vacuum
  7. extractionthe mixture is extracted with DCM
  8. dry with materialthe organic phase is dried over sodium sulphate
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-ce4974ec3f6c46f3a515a926a96f07d3
Source dataset
uspto-grants-1997_08
Patent number
US05656648

Reaction notes

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