Sodium Azide → HCID 86666732, compound

HRID 2401439Notes

Reaction equation

HRID 2401439 reaction equation
CS(O[CH2:6][C:7]1[O:11][N:10]=[C:9]([CH3:12])[C:8]=1[C:13]1[C:14]([C:19](=[O:27])[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[N:15][N:16]([CH3:18])[CH:17]=1)(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C)C=O>[N:28]([CH2:6][C:7]1[O:11][N:10]=[C:9]([CH3:12])[C:8]=1[C:13]1[C:14]([C:19]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:27])=[N:15][N:16]([CH3:18])[CH:17]=1)=[N+:29]=[N-:30]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86666731HCID 86666731, compound

Product 1

HCID 86666732HCID 86666732, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4-(3-(4-chlorobenzoyl)-1-methyl-1H-pyrazol-4-yl)-3-methylisoxazol-5-yl)methyl methanesulfonate (35 mg, 0.09 mmol), sodium azide (12 mg, 0.18 mmol) in N,N-dimethylformamide (10 mL) was heated to 80° C. and stirred for 10 h. After cooling to room temperature, the mixture was concentrated, and the residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate=1:3 to give the titled product as a colorless oil (30 mg, 94%). LC/MS: m/z 356 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.16 (d, J=9 Hz, 2H), 7.50 (s, 1H), 7.46 (d, J=9 Hz, 2H), 4.37 (s, 2H), 4.09 (s, 3H), 2.19 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with petroleum ether/ethyl acetate=1:3

Sources & evidence

ORD record
ord-4d8ab02439274190a3a700e275a826ab
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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