2-Aminothiazole → HCID 178439954, compound

HRID 2419817Notes

Reaction equation

HRID 2419817 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19](O)=[O:20].[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[S:24]1[CH:25]=[CH:26][N:27]=[C:23]1[NH:22][C:19]([C:3]1[C:4]([CH:16]([CH3:18])[CH3:17])=[N:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]([F:15])([F:14])[F:13])=[O:20]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 10868DicyclohexylcarbodiimideHCID 178439957HCID 178439957, compound

Product 1

HCID 178439954HCID 178439954, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.3 g of the product of Step E, 2.1 g of 2-aminothiazole, 4.74 g of dicyclohexylcarbodiimide and 130 ml of dimethylformamide was stirred for 72 hours and was then filtered. The filtrate was evaporated to dryness and the residue was taken up in 50 ml of a 5% sodium bicarbonate solution. The mixture was filtered and washed with water until the wash water were neutral to obtain 8 g of raw product. The latter was chromatographed and was eluted with a 9-1 methylene chloride-ethyl acetate to recover the fraction with an Rf = 0.25. The product was dried to obtain 6 g of product which was crystallized from acetone to obtain 4.2 g of N-(3-thiazolyl)-4-hydroxy-2-isopropyl-8-trifluoromethyl-quinoline-3-carboxamide in the form of colorless crystals melting at 213° C.

Workup

  1. filtrationwas then filtered
  2. customThe filtrate was evaporated to dryness
  3. filtrationThe mixture was filtered
  4. washwashed with water until the wash water
  5. customto obtain 8 g of raw product
  6. customThe latter was chromatographed
  7. washwas eluted with a 9-1 methylene chloride-ethyl acetate
  8. customto recover the fraction with an Rf = 0.25
  9. customThe product was dried

Sources & evidence

ORD record
ord-5a47b8f670444443b33c4f2081b1e9de
Source dataset
uspto-grants-1978_08
Patent number
US04107310

Reaction notes

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