Acetic Anhydride → HCID 59737275, compound

HRID 1907765Notes

Reaction equation

HRID 1907765 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:36]=[CH:35][C:10]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH:17]=[CH:18][C:19]=3[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>N1C=CC=CC=1>[C:37]([NH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[CH:17]=[CH:18][C:19]=3[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:12])=[CH:35][CH:36]=2)[CH2:3]1)(=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59737269HCID 59737269, compound

Product 1

HCID 59737275HCID 59737275, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 404 (0.295 g, 0.601 mmol) in pyridine (3.0 mL) under nitrogen was added acetic anhydride (1.59 mL, 16.84 mmol), and the mixture was stirred for 19 h at room temperature. The solvent was evaporated and the residue obtained was evaporated twice with toluene and triturated with a mixture of Et2O and hexanes. The solid was filtered, air-dried and then dried under vacuum to afford the title compound 407 as a light pink solid (280 mg, 85%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue obtained
  3. customwas evaporated twice with toluene
  4. customtriturated with a mixture of Et2O and hexanes
  5. filtrationThe solid was filtered
  6. customair-dried
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6ef2f40e476646f68c00386d3bfa1236
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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