Sodium Hydroxide → HCID 178424679, compound

HRID 1958668Notes

Reaction equation

HRID 1958668 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]#[N:5].[N-:33]=[N+:34]=[N-:35].[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]1[NH:35][N:34]=[N:33][N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 44545795HCID 44545795, compound

Product 1

HCID 178424679HCID 178424679, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 76) (100 mg, 0.238 mmol) and sodium azide (20.9 mg, 0.321 mmol) in toluene (1 mL) was stirred at 120° C. for overnight. The reaction mixture was cooled to room temperature and basified to pH 9-10 with 5N NaOH solution in the ice bath. The mixture was extracted with CH2Cl2 (5 mL, 3 times), and then the aqueous layer was acidified to pH 4 with 2N HCl solution. The precipitate was filtered, washed with H2O, and dried under vacuum for overnight to afford the solid, which was recrystallized from MeOH/CH2Cl2/Et2O to give the title compound (56 mg, 51%). (300 MHz, CDCl3+CD3OD) δ 2.49 (3H, s), 4.17 (2H, s), 6.98 (1H, d), 7.08 (1H, dd), 7.13 (1H, d), 7.35-7.41 (2H, m), 7.45-7.50 (1H, m), 7.81 (1H, dd), 7.97-8.01 (2H, m), 8.05 (1H, d), 8.13 (1H, dd), 8.80 (1H, dd). MS (ESI) m/z 463 (MH+).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (5 mL, 3 times)
  2. filtrationThe precipitate was filtered
  3. washwashed with H2O
  4. customdried under vacuum for overnight
  5. customto afford the solid, which
  6. customwas recrystallized from MeOH/CH2Cl2/Et2O

Sources & evidence

ORD record
ord-3932f3cd26424ec68f4bf6f1d59ce6cc
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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