Acetic Anhydride → HCID 25234839, compound

HRID 2360039Notes

Reaction equation

HRID 2360039 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([N:23]4[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]4=[O:30])[CH:14]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]=3[O:17][CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>>[C:19]([C:15]1[C:16]([O:17][CH3:18])=[C:11]([C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:31](=[O:33])[CH3:32])[S:3][C:4]=3[CH:10]=2)[CH:12]=[C:13]([N:23]2[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]2=[O:30])[CH:14]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 25234760HCID 25234760, compound

Product 1

HCID 25234839HCID 25234839, compoundYield 88%

Conditions

Temperature
100 °C

Procedure

A mixture of the product from Example 83 (30 mg, 0.071 mmol) and acetic anhydride (3 mL) was stirred at 100° C. for 2 h, and then allowed to cool to room temperature. The resulting solid was collected by filtration, washed with H2O, and dried to give the title compound as an off-white solid (29 mg, 88%). 1H NMR (300 MHz, DMSO-d6) δ 12.42 (s, 1H) 11.41 (d, J=2.21 Hz, 1H) 8.12 (d, J=1.47 Hz, 1H) 7.82 (d, J=8.46 Hz, 1H) 7.78 (d, J=8.09 Hz, 1H) 7.61 (dd, J=8.46, 1.84 Hz, 1H) 7.31 (q, J=2.70 Hz, 2H) 5.64 (dd, J=8.09, 2.21 Hz, 1H) 3.24 (s, 3H) 2.22 (s, 3H) 1.41 (s, 9H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-4a59c4a57b21459da210757f79f0aa93
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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