Ammonia → HCID 71270783, compound

HRID 510389Notes

Reaction equation

HRID 510389 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:23])[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=3[CH3:22])=[C:6]2[N:5]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:3]=1.[NH3:30]>CO>[CH3:23][C:9]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=2[CH3:22])=[C:6]2[N:5]=[C:4]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:3]=[C:2]([NH2:30])[N:7]2[N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86724878HCID 86724878, compound

Product 1

HCID 71270783HCID 71270783, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 7-chloro-2-methyl-3-{{2-methyl-3-(trifluoromethyl)phenyl}methyl}-5-(4-morpholinyl)pyrazolo[1,5-a]pyrimidine (70 mg, 0.16 mmol) in methanol (2 mL) stirred under nitrogen at 0° C. was added a 2 M ammonia solution of in CH3OH (0.82 mL, 1.64 mmol) dropwise. The reaction mixture was stirred at 135° C. for 3 hours. Reaction mixture was concentrated to dryness. Crude product was purified by reverse-phase HPLC to provide titled compound. (16 mg, 24%); LC/MS: MS (ES+) m/e 406 (MH+); 1H NMR (400 MHz, MeOD) δ ppm 2.20 (s, 3H) 2.52 (s, 3H) 3.15 (dt, J=3.28, 1.64 Hz, 1H) 3.50 (dt, J=3.28, 1.64 Hz, 1H) 3.57 (d, J=5.31 Hz, 3H) 3.55 (s, 1H) 3.82 (s, 1H) 3.81 (d, J=5.05 Hz, 3H) 4.10 (s, 2H) 5.59 (s, 1H) 7.12 (s, 1H) 7.26 (s, 1H) 7.55 (s, 1H).

Workup

  1. stirringThe reaction mixture was stirred at 135° C. for 3 hours
  2. customReaction mixture
  3. concentrationwas concentrated to dryness
  4. customCrude product was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-fa215c317cb84fd59193d4bf75706012
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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