Triethylamine → 2-[(1-Acetyl-2-indolyl)carbonylamino]-4-(2,4-dimethoxyphenyl)-5-ethoxycarbonylmethylthiazole

HRID 1769102Notes

Reaction equation

HRID 1769102 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[O:15][CH3:16])[N:6]=1.[C:23]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[C:35](O)=[O:36])(=[O:25])[CH3:24].C(N(CC)CC)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>ClCCl>[C:23]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[C:35]([NH:1][C:2]1[S:3][C:4]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[O:15][CH3:16])[N:6]=1)=[O:36])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 102198671-acetylindole-2-carboxylic AcidHCID 189465712-Amino-4-(2,4-dimethoxyphenyl)-5-ethoxycarbonylmethylthiazole

Product 1

HCID 189465652-[(1-Acetyl-2-indolyl)carbonylamino]-4-(2,4-dimethoxyphenyl)-5-ethoxycarbonylmethylthiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g of 2-amino-4-(2,4-dimethoxyphenyl)-5-ethoxycarbonylmethylthiazole, 1 g of 1-acetylindole-2carboxylic acid, 0.7 ml of triethylamine and 2.39 g of BOP are dissolved in 15 ml of dichloromethane. The reaction mixture is stirred overnight at room temperature and then concentrated under vacuum. The residue is taken up in ethyl acetate and the solution is successively washed with a buffer solution, pH=2, with a 5% solution of NaHCO3 and with water, and then the organic phase is dried over MgSO4 and concentrated under vacuum. The residue is purified by chromatography on a silica gel, eluent: dichloromethane/ethyl acetate 100/2.5 (v/v).

Workup

  1. concentrationconcentrated under vacuum
  2. washthe solution is successively washed with a buffer solution, pH=2, with a 5% solution of NaHCO3 and with water
  3. dry with materialthe organic phase is dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by chromatography on a silica gel, eluent

Sources & evidence

ORD record
ord-7ff815a8f92f4e508c8ccc0a5f2a4474
Source dataset
uspto-grants-1995_01
Patent number
US05380736

Reaction notes

Loading…