Acetic Anhydride → HCID 58504508, compound

HRID 2367194Notes

Reaction equation

HRID 2367194 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([F:16])[CH:9]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>CN(C1C=CN=CC=1)C>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([C:6]2[CH:5]=[C:4]([N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[N:3]=[C:2]([NH:1][C:23](=[O:25])[CH3:24])[N:7]=2)=[CH:9][C:10]=1[F:16])#[N:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 51356850HCID 51356850, compound

Product 1

HCID 58504508HCID 58504508, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst2×

Conditions

Temperature
95 °C

Procedure

In a 25 mL sealable tube under argon were combined 4-[2-amino-6-(1-piperidinyl)-4-pyrimidinyl]-2-fluorobenzonitrile (0.18 g, 0.44 mmol) and acetic anhydride (5 mL). The vial was sealed and the reaction mixture was stirred at 95° C. After 16 hours, LCMS indicated a mixture of 2:1 bis:mono acetylated products. The reaction mixture was cooled to room temperature and concentrated. To the resulting crude mixture (192 mg) was added CH3OH (10 mL) followed by DMAP (0.046 g, 0.38 mmol) and the reaction mixture was stirred overnight at 30° C. Additional DMAP (30 mg) was added and the reaction mixture was stirred for an additional 24 hours. The reaction was concentrated, and the resulting oil was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compound (150 mg, some DMAP is present) as a light yellow solid. LC-MS (ES) m/z=340 [M+H]+.

Workup

  1. customIn a 25 mL sealable tube under argon were combined
  2. customThe vial was sealed
  3. additiona mixture of 2:1 bis
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated
  6. additionTo the resulting crude mixture (192 mg) was added CH3OH (10 mL)
  7. stirringthe reaction mixture was stirred overnight at 30° C
  8. stirringthe reaction mixture was stirred for an additional 24 hours
  9. concentrationThe reaction was concentrated
  10. customthe resulting oil was partitioned between EtOAc and water
  11. customThe organic layer was separated
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-0f45b424d63b4603972c3ce90ec1b88d
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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