Acetic Anhydride → HCID 71272066, compound

HRID 510390Notes

Reaction equation

HRID 510390 reaction equation
[CH3:1][C:2]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[C:20]=2[CH3:29])=[C:5]2[N:6]=[C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:8]=[C:9]([NH2:10])[N:4]2[N:3]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>CN(C=O)C>[CH3:1][C:2]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[C:20]=2[CH3:29])=[C:5]2[N:6]=[C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:8]=[C:9]([NH:10][C:30](=[O:32])[CH3:31])[N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 71270783HCID 71270783, compound

Product 1

HCID 71272066HCID 71272066, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-5-(4-morpholinyl)pyrazolo[1,5-a]pyrimidin-7-amine (120 mg, 0.3 mmol), prepared as described in Example 17, in DMF (1 mL) was added acetic anhydride (30 mg, 0.3 mmol). Reaction mixture was stirred overnight. Reaction mixture was concentrated to dryness and dissolved with DMSO (1 mL). The crude product was purified by reversed phase HPLC to provide the titled compound (15 mg, 11%); LC/MS: MS (ES+) m/e 448 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H) 2.30 (s, 3H) 2.44-2.48 (m, 3H) 3.38-3.50 (m, 4H) 3.61-3.70 (m, 4H) 3.95 (s, 2H) 7.20 (s, 1H) 7.28 (d, J=7.83 Hz, 1H) 7.37 (d, J=7.07 Hz, 1H) 7.51 (d, J=7.83 Hz, 1H) 10.60 (s, 1H).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. concentrationwas concentrated to dryness
  4. dissolutiondissolved with DMSO (1 mL)
  5. customThe crude product was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-50e716d197924c8ea08b87eb99b70cbb
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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