Diisopropylethylamine → HCID 58477342, compound

HRID 876545Notes

Reaction equation

HRID 876545 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=2)[O:5][C:4]([C:15]2[C:16]([C:21]([F:24])([F:23])[F:22])=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:3]1.[CH3:25][C:26]1[S:30][C:29]([NH2:31])=[N:28][CH:27]=1.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>[CH3:25][C:26]1[S:30][C:29]([NH:31][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[O:5][C:4]([C:15]2[C:16]([C:21]([F:24])([F:22])[F:23])=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:3][C:2]3=[O:1])=[O:14])=[N:28][CH:27]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3517702-Amino-5-methylthiazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58477232HCID 58477232, compound

Product 1

HCID 58477342HCID 58477342, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-oxo-2-(2-(trifluoromethyl)pyridin-3-yl)-4H-chromene-8-carboxylic acid 41 (210 mg, 0.6 mmol), 5-methyl-1,3-thiazole-2-ylamine 47 (68 mg, 0.6 mmol), HATU (274 mg, 0.72 mmol), and DIPEA (155 mg, 1.2 mmol) in DMF (4 mL) was stirred at 55° C. for 12 h. The reaction mixture was poured into H2O (25 mL) and extracted with ethyl acetate. The organic layer was concentrated and purified by flash chromatography to give Compound 305 (85 mg, 32% yield). MS (ESI) calcd for C20H12F3N3O3S: 431.06. found: 432 [M+H].

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-10dc9d1f60df48fc9c365261cbb5f82f
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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