Acetic Anhydride → Methyl 6-[(acetylamino)methyl]-5-chloro-2-(3-fluorophenyl)nicotinate

HRID 717825Notes

Reaction equation

HRID 717825 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]([Cl:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:4]=1.C(N(CC)C(C)C)(C)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>CN(C)C=O>[C:30]([NH:1][CH2:2][C:3]1[C:12]([Cl:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:4]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 58515976Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate

Product 1

HCID 58515958Methyl 6-[(acetylamino)methyl]-5-chloro-2-(3-fluorophenyl)nicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate (0.35 g, 1,2 mmol) was stirred in N,N-dimethylformamide (5 mL) with N,N-diisopropylethylamine (0.41 mL, 2.4 mmol) and acetic anhydride (0.17 mL, 1.8 mmol) was added. The mixture was stirred for 30 minutes at room temperature. Evaporation gave the crude material which was contaminated with the corresponding dechlorinated byproduct (0.4 g, 100%). LCMS calculated for C16H15ClFN2O3 (M+H)+: m/z=337.1. found 336.9.

Workup

  1. additionwas added
  2. customEvaporation

Sources & evidence

ORD record
ord-c22f401b74c247c3bb4424009b0356fe
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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