Nicotinoyl chloride → HCID 67298051, compound

HRID 1520377Notes

Reaction equation

HRID 1520377 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>C1COCC1.CCN(CC)CC>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:2]([NH:1][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=2)=[C:3]([C:4](=[O:5])[NH2:6])[CH:7]=1

Participants

5

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 58540804HCID 58540804, compound

Product 1

HCID 67298051HCID 67298051, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-amino-5-bromo-3-methylbenzamide (820 mg, 3.55 mmol, 1.0 eq.) in THF (15 mL) and Et3N (0.7 nit) was added nicotinoyl chloride (551 mg, 3.91 mmol, 1.1 eq.) in anhydrous THF (15 mL) dropwise. The resulting mixture was stirred at room temperature overnight. After the reaction was completed, the resultant precipitate was filtered and dried in vacuo to give 1.74 g of crude iii-e as a yellow solid. LCMS m/z=333.8, 335.8 (M+1) (Method B) (retention time=1.42 min).

Workup

  1. filtrationthe resultant precipitate was filtered
  2. customdried in vacuo
  3. customto give 1.74 g of crude iii-e as a yellow solid

Sources & evidence

ORD record
ord-c21fc7cb124c4d489352ce84eeeea422
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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