Ammonium Chloride → 5-Cyano-2-(difluoromethyl)nicotinamide
Reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]([CH:12]([F:14])[F:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9])#[N:2].C[N:16](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[N:5][C:6]([CH:12]([F:14])[F:13])=[C:7]([CH:11]=1)[C:8]([NH2:16])=[O:9])#[N:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-cyano-2-(difluoromethyl)nicotinic acid (0.600 g, 3.0 mmol) in dry DMF (20 mL), TBTU (10.0 g, 3.33 mmol) was added at 0° C. followed by slow addition of DIPEA (0.7 mL, 3.93 mmol). The reaction mass was stirred at 0° C. for 1 h and ammonium chloride (3.33 g, 60.7 mmol) was added. The reaction mass was stirred at RT for 30-48 h. After completion of reaction quenched the reaction mass with DCM, filtered off solid to afford 0.500 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 8.16 (m, 1H), 8.63 (s, 1H), 9.22 (s, 1H).
Workup
- stirringThe reaction mass was stirred at RT for 30-48 h
- customAfter completion of reaction
- customquenched the reaction mass with DCM
- filtrationfiltered off solid
Sources & evidence
- ORD record
- ord-46593c134b0d49ffb87b7a5577acdb6b
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09439890B2
Reaction notes
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