Acetic Anhydride → HCID 67443228, compound

HRID 1400828Notes

Reaction equation

HRID 1400828 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH2:30][NH:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:26][CH:25]=5)[S:23][C:16]=34)=[C:10]([F:36])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1.[CH3:37][C:38](OC(C)=O)=[O:39]>N1C=CC=CC=1>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:32][CH2:33][O:34][CH3:35])[C:38](=[O:39])[CH3:37])=[CH:26][CH:25]=5)[S:23][C:16]=34)=[C:10]([F:36])[CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68224035HCID 68224035, compound

Product 1

HCID 67443228HCID 67443228, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 113 (100 mg, 0.197 mmol) in pyridine (3 mL) was added Ac2O (30.2 mg, 0.296 mmol) and the reaction mixture was stirred for an hour. The mixture was concentrated then re-dissolved in EtOAc and washed with saturated CuSO4 solution then water. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid was triturated with Et2O to afford title compound 114 (97 mg, 90% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.68 (s, 1H), 8.48 (m, 1H), 8.03 (s, 1H, rotamer), 7.83 (m, 2H, rotamer), 7.70 (m, 1H), 7.36 (m, 3H), 7.18 (m, 1H), 6.56 (m, 2H), 4.57 (s, 2H, rotamer) 3.43 (s, 3H), 3.29 (s, 2H), 3.20 (s, 2H, rotamer), 2.49 (m, 1H), 2.06 (s, 3H, rotamer), 0.63 (m, 2H), 0.41 (m, 2H). MS (m/z)=549.57 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in EtOAc
  3. washwashed with saturated CuSO4 solution
  4. customThe organic phase was collected
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resultant solid was triturated with Et2O

Sources & evidence

ORD record
ord-08a3f9c0eb8f41039a2ee3165bd5f705
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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