Acetyl chloride → HCID 69219663, compound

HRID 272677Notes

Reaction equation

HRID 272677 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:9]=3[C:8](=[O:17])[NH:7][C:6]=2[CH:18]=1.[C:19](Cl)(=[O:21])[CH3:20]>N1C=CC=CC=1>[Cl:16][C:13]1[CH:14]=[CH:15][C:9]2[C:8](=[O:17])[NH:7][C:6]3[CH:18]=[C:2]([NH:1][C:19](=[O:21])[CH3:20])[CH:3]=[CH:4][C:5]=3[NH:11][C:10]=2[CH:12]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 69217462HCID 69217462, compound

Product 1

HCID 69219663HCID 69219663, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 7C (100 mg, 0.38 mmol) in pyridine (10 mL) at 0° C. was treated with acetyl chloride (32 mg, 0.40 mmol), stirred overnight, and concentrated. The residue was purified by flash column chromatography on silica gel with ethyl acetate to provide 64 mg (56%) of the desired product. MS (DCI) m/e 302 (M+H)+, 319 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 9.93 (s, 1H), 9.81 (s, 1H), 7.93 (s, 1H), 7.67 (d, J=8.4 Hz, 1H), 7.25 (d, J=1.9 Hz, 1H), 7.16 (dd, J=8.4, 2.2 Hz, 1H), 7.05 (d, J=1.9 Hz, 1H), 6.90 (dd, J=8.4, 1.9 Hz, 1H), 6.88 (d, J=8.7 Hz, 1H), 1.99 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-fe4928ce05f746dc9b000410a1a9e8ab
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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