Ammonium Chloride → HCID 178433735, compound

HRID 510450Notes

Reaction equation

HRID 510450 reaction equation
[CH3:1][C:2]1[C:18]([CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[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-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][C:2]1[C:18]([CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[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[NH:32][N:31]=[N:30][N:11]=3)[N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium AzideHCID 71270855HCID 71270855, compound

Product 1

HCID 178433735HCID 178433735, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 5 mL microwave vial was added in 2-methyl-5-(4-morpholinyl)-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine-7-carbonitrile (60 mg, 0.156 mmol), sodium azide (81 mg, 1.252 mmol) and ammonium chloride (67.0 mg, 1.252 mmol) in N,N-Dimethylformamide (DMF) (2 mL). The reaction was subjected to MW 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 (0˜10% MeOH/DCM) to give the titled product (22 mg, 31%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H) 3.70 (m, 8H) 4.38 (s, 2H) 7.12 (br. s., 1H) 7.29-7.45 (m, 2H) 7.47-7.57 (m, 2H) 7.77 (d, J=8.08 Hz, 1H) 7.85-7.96 (m, 1H) 8.49 (m, 1H); LC/MS: MS (ES+) m/e 427.0 [M+H]+.

Workup

  1. customThe reaction was subjected to MW irradiation 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-fa6eb1e106da4a489e7e2ed6639e98e2
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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