Triethylamine → HCID 21249511, compound

HRID 2082406Notes

Reaction equation

HRID 2082406 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:6]=1.[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]1[C:25](O)=[O:26].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>CN(C)C=O>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([NH:1][C:25]([C:17]3[N:16]([CH3:15])[C:24]4[C:19]([CH:18]=3)=[CH:20][CH:21]=[CH:22][CH:23]=4)=[O:26])[S:3][CH:4]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1596442-Amino-4-(4-methoxyphenyl)thiazole

Product 1

HCID 21249511HCID 21249511, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of 2-amino-4-(4-methoxyphenyl)thiazole is dissolved in 20 ml of dimethylformamide and, successively, 0.6 g of 1-methylindole-2-carboxylic acid, then 1.6 g of 1-benzotriazolyl-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and then 0.7 g of triethylamine are added to the reaction mixture at ambient temperature. The reaction mixture is left at ambient temperature for about 12 hours, while stirring well, before pouring into 100 ml of ice-water; the aqueous phase obtained is then extracted with twice 50 ml of ethyl acetate. The organic extracts are dried over anhydrous magnesium sulphate and evaporated to dryness. The residual solid is purified by chromatography on a silica column (eluant: CH2Cl2). Yield

Workup

  1. customthe aqueous phase obtained
  2. extractionis then extracted with twice 50 ml of ethyl acetate
  3. dry with materialThe organic extracts are dried over anhydrous magnesium sulphate
  4. customevaporated to dryness
  5. customThe residual solid is purified by chromatography on a silica column (eluant: CH2Cl2)
  6. customYield

Sources & evidence

ORD record
ord-a8f746cf51124fb59b56d62f31b823ff
Source dataset
uspto-grants-1993_02
Patent number
US05189049

Reaction notes

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