Pyridine → HCID 66789824, compound

HRID 1929422Notes

Reaction equation

HRID 1929422 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14]3[CH:15]=[CH:16][C:17]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]=3[O:12][C:11]([CH3:25])([CH3:24])[C:10]2=[O:26])[CH:5]=[CH:6][C:7]=1[F:8].N1C=CC=CC=1.[C:33](Cl)(=[O:35])[CH3:34]>ClCCl>[CH3:25][C:11]1([CH3:24])[C:10](=[O:26])[N:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][C:33](=[O:35])[CH3:34])[CH:3]=2)[C:14]2[CH:15]=[CH:16][C:17]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]=2[O:12]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 66789441HCID 66789441, compound

Product 1

HCID 66789824HCID 66789824, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[4-(3-amino-4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide (compound obtained in Example 44; 13 mg) and pyridine (5.5 μL) in dichloromethane (5 mL) was added acetyl chloride (3.6 μL) under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was purified by column chromatography on silica gel (solvent; chloroform to chloroform/methanol (9/1) and triturated with diisopropylether to give N-(5-{2,2-dimethyl-7-[(methanesulfonyl)amino]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl}-2-fluorophenyl)acetamide (10 mg) as a pale yellow powder.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was purified by column chromatography on silica gel (solvent
  3. customchloroform to chloroform/methanol (9/1) and triturated with diisopropylether

Sources & evidence

ORD record
ord-13be4a5d1ced4749b72c12806bfd41c8
Source dataset
uspto-grants-2012_05
Patent number
US08188073B2

Reaction notes

Loading…