Sodium Azide → HCID 58674469, compound

HRID 1994140Notes

Reaction equation

HRID 1994140 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]#[N:26])[CH:20]=3)=[CH:14][CH:13]=2)=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].[Cl-].[Cl-].[Cl-].[Al+3].[N-:36]=[N+:37]=[N-:38].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[N:36]=[N:37][NH:38][N:26]=4)[CH:20]=3)=[CH:14][CH:13]=2)=[CH:4][C:3]=1[C:28]([F:31])([F:29])[F:30]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 58674292HCID 58674292, compound

Product 1

HCID 58674469HCID 58674469, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-3-{4-[(2-cyanopyridin-4-yl)oxy]phenyl}propanamide (0.300 g, 0.67 mmol), aluminum trichloride (1.0 M in hexanes, 2.0 mL, 2.0 mmol), and sodium azide (0.131 g, 2.0 mmol) in DMF was heated at 100° C. for 3 days. The mixture was concentrated and purified by column chromatography to give A-57 which was converted to the bishydrochloride salt (29 mg). 1H NMR (400 MHz, CD3OD; bis HCl salt) δ: 8.66 (d, 1H), 8.03 (d, 1H), 7.93 (d, 1H), 7.66 (dd, 1H), 7.52 (t, 1H), 7.45 (d, 1H), 7.41 (dd, 1H), 7.37 (d, 1H), 7.21-7.24 (m, 1H), 7.12-7.17 (m, 1H), 3.10 (t, 2H), and 2.75 (t, 2H). LCMS, FA: Rt=1.48 min, [MH+ 489.3].

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography
  3. customto give A-57 which

Sources & evidence

ORD record
ord-bb30cf7eb38543cba6ec2b983758c2e2
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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