Dimethylformamide → HCID 67304388, compound

HRID 2278732Notes

Reaction equation

HRID 2278732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:10]=1)[C:5]([OH:7])=O.[CH3:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25][NH2:26])=[CH:21][CH:20]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CN(C)C=O>[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:10]=1)[C:5]([NH:26][CH2:25][C:22]1[CH:23]=[N:24][C:19]([CH3:18])=[CH:20][CH:21]=1)=[O:7]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12214337(6-Methylpyridin-3-yl)methanamineHCID 58449374HCID 58449374, compound

Product 1

HCID 67304388HCID 67304388, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A round bottom flask was charged with 3-bromo-5-(5-methylpyridin-2-yl)benzoic acid (450.00 mg, 1.5404 mmol), (6-methylpyridin-3-yl)methanamine (225.83 mg, 1.8485 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1171.4 mg, 3.0808 mmol), N,N-diisopropylethylamine (0.93910 mL, 5.3915 mmol) and N,N-dimethylformamide (5.00 mL, 64.6 mmol) and the reaction stirred at room temperature for 1 hour. The reaction was poured into brine and extracted with ethyl acetate to get the product as brown solid

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-20f64d4680cb43d2b4718cabc50d1c94
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

Loading…