Triethylamine → 2-[(2-Indolyl)carbonylamino]-5-methoxy-4-phenylthiazole

HRID 1034190Notes

Reaction equation

HRID 1034190 reaction equation
[NH2:1][C:2]1[S:3][C:4]([O:13][CH3:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[C:27](O)=[O:28])(=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(N(CC)CC)C>C(Cl)Cl.O>[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[C:27]([NH:1][C:2]1[S:3][C:4]([O:13][CH3:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1)=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 102198671-acetylindole-2-carboxylic AcidHCID 189465662-Amino-5-methoxy-4-phenylthiazole

Product 1

HCID 189465772-[(2-Indolyl)carbonylamino]-5-methoxy-4-phenylthiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3.15 g of 2-amino-5-methoxy-4-phenylthiazole are dissolved in 60 ml of CH2Cl2. 3.26 g of 1-acetylindole-2-carboxylic acid, 8.12 g of BOP and 1.86 g of triethylamine are added, and the reaction mixture is stirred at room temperature for one week. 50 ml of water are added and the organic phase is decanted, dried over Na2SO4, filtered and concentrated under vacuum. The residue is taken up in 100 ml of methanol, and 10 g of K2CO3 are added and the mixture is stirred overnight at room temperature. The mixture is concentrated under vacuum, and the residue is taken up in water, and the precipitate formed is separated by filtration and washed with CH2Cl2.

Workup

  1. customthe organic phase is decanted
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. addition10 g of K2CO3 are added
  6. stirringthe mixture is stirred overnight at room temperature
  7. concentrationThe mixture is concentrated under vacuum
  8. customthe precipitate formed
  9. customis separated by filtration
  10. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-dbeaf22b1f384d299c60486d6bce4de4
Source dataset
uspto-grants-1994_05
Patent number
US05314889

Reaction notes

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