Sodium Azide → HCID 178472411, compound

HRID 2202750Notes

Reaction equation

HRID 2202750 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:42])[CH2:9][N:10]([CH2:33][C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[C:36]([F:41])[CH:35]=2)[C:11]([C:13]2[CH:14]=[N:15][N:16]([C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]3)[C:17]=2[C:18]([F:21])([F:20])[F:19])=[O:12])=[C:6]([Cl:43])[CH:5]=[CH:4][N:3]=1.[N-:44]=[N+:45]=[N-:46].[Na+]>CN(C=O)C>[N:44]([C:2]1[C:7]([C:8](=[O:42])[CH2:9][N:10]([CH2:33][C:34]2[CH:35]=[C:36]([F:41])[CH:37]=[C:38]([F:40])[CH:39]=2)[C:11]([C:13]2[CH:14]=[N:15][N:16]([C@H:22]3[CH2:23][CH2:24][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:27]3)[C:17]=2[C:18]([F:20])([F:21])[F:19])=[O:12])=[C:6]([Cl:43])[CH:5]=[CH:4][N:3]=1)=[N+:45]=[N-:46]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178472409HCID 178472409, compound

Product 1

HCID 178472411HCID 178472411, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl trans-4-(4-((2-(2,4-dichloropyridin-3-yl)-2-oxoethyl)(3,5-difluorobenzyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)cyclohexanecarboxylate (100 mg, 0.15 mmol) in DMF (5 mL) was added NaN3 (50 mg, 0.7 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 30% EtOAc/hexane as eluent) to provide compound 21-1 (60 mg, 59%) as a brown oil.

Workup

  1. customThe reaction mixture was quenched with water (20 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, 30% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-37d51753078849d29be56ac0221cd9dd
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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