Sodium Azide → HCID 86684773, compound

HRID 579201Notes

Reaction equation

HRID 579201 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:8][C:9]=1[N:10]1[CH:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:13][C@H:12](Br)[C:11]1=[O:23])=[O:4].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:8][C:9]=1[N:10]1[CH:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:13][C@H:12]([N:30]=[N+:31]=[N-:32])[C:11]1=[O:23])=[O:4]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 66684104HCID 66684104, compound

Product 1

HCID 86684773HCID 86684773, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To the solution of 3-((S)-3-bromo-6-cyclohexyl-2-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (78 mg, 0.16 mmol, 1 equiv.) in DMF (1.0 mL) was added NaN3 (12 mg, 0.19 mmol, 1.2 equiv) and the resulting mixture was stirred at 65° C. for 18 hours. The solvent was then removed under vacuum. The residue was purified by silica gel column chromatography (EtOAc/Heptane, 10%˜60%) to give product 42 mg (yield 56%). MS: 442 [M+H+].

Workup

  1. customThe solvent was then removed under vacuum
  2. customThe residue was purified by silica gel column chromatography (EtOAc/Heptane, 10%˜60%)

Sources & evidence

ORD record
ord-eb544e69f5854ed4a2907c7ccebaa80f
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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