2-Aminothiazole → HCID 58154706, compound

HRID 2359426Notes

Reaction equation

HRID 2359426 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:16]=[CH:15][C:14]3[C:9](=[C:10]([C:17]([OH:19])=O)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=1.[S:20]1[CH:24]=[CH:23][N:22]=[C:21]1[NH2:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:16]=[CH:15][C:14]3[C:9](=[C:10]([C:17]([NH:25][C:21]4[S:20][CH:24]=[CH:23][N:22]=4)=[O:19])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58154615HCID 58154615, compound

Product 1

HCID 58154706HCID 58154706, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(pyridin-3-yl)quinazoline-8-carboxylic acid (250 g, 1.0 mmol), thiazole-2-amine (94 mg, 1.0 mmol), HATU (760 mg, 2.0 mmol) and DIPEA (260 mg, 2.0 mmol) in DMF (15 mL) was stirred at 50° C. for 12 hours. Water (20 mL) was added and the precipitate was collected by filtration, washed with water (3×10 mL) and methanol (3×5 mL) to obtain 2-(pyridin-3-yl)-N-(thiazol-2-yl)quinazoline-8-carboxamide (150 mg, 46% yield). MS (ESI) calcd for C17H11N5OS (m/z): 333.07. found: 334 [M+1].

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water (3×10 mL) and methanol (3×5 mL)

Sources & evidence

ORD record
ord-b640393b251640298768f6a891053dd4
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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