Ammonium Chloride → HCID 71272303, compound

HRID 510448Notes

Reaction equation

HRID 510448 reaction equation
[CH3:1][C:2]1[C:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:21]=2[CH3:30])=[C:5]2[N:6]=[C:7]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:8]=[C:9]([C:10]#[N:11])[N:4]2[N:3]=1.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][C:2]1[C:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[C:21]=2[CH3:30])=[C:5]2[N:6]=[C:7]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:8]=[C:9]([C:10]3[N:31]=[N:32][NH:33][N:11]=3)[N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium AzideHCID 71270957HCID 71270957, compound

Product 1

HCID 71272303HCID 71272303, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 5 mL microwave vial was added in 2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-5-(4-morpholinyl)pyrazolo[1,5-a]pyrimidine-7-carbonitrile (68 mg, 0.164 mmol), sodium azide (85 mg, 1.310 mmol) and ammonium chloride (70.0 mg, 1.310 mmol) in N,N-Dimethylformamide (DMF) (1 mL). The reaction was subjected to microwave irradiation at 180° C. for 15 min. The reaction mixture was added to a saturated NH4Cl solution and extracted with DCM (30 mL×2). The combined organic phases were dried and concentrated. The residue was purified on silica column (20˜60% EtOAc/Hexane) and then (5% MeOH/DCM) to give the titled product (32 mg, 41%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.29 (s, 3H) 2.46 (s, 3H) 3.47-3.79 (m, 8H) 4.01 (s, 2H) 7.15-7.34 (m, 2H) 7.40 (d, J=8.15 Hz, 1H) 7.53 (d, J=7.74 Hz, 1H); LC/MS: MS (ES+) m/e 459.3 [M+H]+.

Workup

  1. customirradiation at 180° C. for 15 min
  2. extractionextracted with DCM (30 mL×2)
  3. customThe combined organic phases were dried
  4. concentrationconcentrated
  5. customThe residue was purified on silica column (20˜60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-d0992154e81046389e0b3773fcc11a87
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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