Sodium Azide → HCID 86638619, compound

HRID 1094496Notes

Reaction equation

HRID 1094496 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH2:21][C:22]4[CH:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH2:21][C:22]4[CH:27]=[C:26]([N:33]=[N+:34]=[N-:35])[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23652719HCID 23652719, compound

Product 1

HCID 86638619HCID 86638619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 200 mg (0.435 mMol) 6-(6-chloro-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide and 50 mg (0.76 mMol) NaN3 in 5 ml DMF is stirred for 2 h at 60° C., giving 6-(6-azido-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (MS: [M+1]+=467). After cooling to rt, 50 mg Pd/C (10%; Engelhard 4505) are added and the mixture is hydrogenated under a H2-atmosphere for 30 min. Filtration through Celite, concentration and chromatography (Combi Flash; CH2Cl2/MeOH 9:1→1:1) gives the title compound: MS: [M+1]+=441; HPLC: tRet=12.3.

Sources & evidence

ORD record
ord-bf0c57ac09bc4a039fe3f61487f2e3a5
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

Loading…