Acetyl chloride → HCID 59853014, compound

HRID 1670286Notes

Reaction equation

HRID 1670286 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][C:10]=2[F:23])[CH:5]=[CH:4][N:3]=1.[C:24](Cl)(=[O:26])[CH3:25]>N1C=CC=CC=1.CCOC(C)=O>[C:24]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[CH:11][C:10]=2[F:23])[CH:5]=[CH:4][N:3]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 2

HCID 6367Acetyl chloride2×HCID 59852856HCID 59852856, compound

Product 1

HCID 59853014HCID 59853014, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tert-butyl 4-(2-aminopyridin-4-yloxy)-3-fluorophenylcarbamate (150 mg, 0.47 mmol) in anhydrous pyridine (0.5 mL) was cooled to 10° C. and treated with acetyl chloride (33 μL, 0.47 mmol) and the mixture stirred for 45 min. An additional portion of acetyl chloride (16 μL, 0.24 mmol) was added to the reaction and stirring continued for 25 min. The mixture was diluted with EtOAc (20 mL), washed with brine, dried (MgSO4) and concentrated under vacuum to give the title compound (115 mg, 68%). 1H NMR (DMSO-d6) δ 10.55 (s, 1H), 9.71 (s, 1H), 8.16 (d, 1H, J=5.5 Hz), 7.63-7.55 (m, 2H), 7.29-7.23 (m, 2H), 6.68-6.63 (m, 1H), 2.02 (s, 3H), 1.48 (s, 9H); MS (ESI+): m/z 362.22 (M+H)+.

Workup

  1. stirringstirring
  2. waitcontinued for 25 min
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-20863772e44a47d78b9e8a7c9cb3e350
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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