Water → HCID 71547617, compound

HRID 1498786Notes

Reaction equation

HRID 1498786 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12](S(C)(=O)=O)[N:11]=[C:10]([C@@H:18]3[CH2:20][C@H:19]3[C:21]3[N:25]([CH3:26])[C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[N:22]=3)[CH:9]=2)[N:3]=1.[C-:31]#[N:32].[Na+].O>CS(C)=O>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:9]=[C:10]([C@@H:18]3[CH2:20][C@H:19]3[C:21]3[N:25]([CH3:26])[C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[N:22]=3)[N:11]=[C:12]([C:31]#[N:32])[N:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 86732046HCID 86732046, compound

Product 1

HCID 71547617HCID 71547617, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of trans-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(methylsulfonyl)pyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (1-6, 750 mg, 1.77 mmol, 1.0 eq) and sodium cyanide (173 mg, 3.54 mmol, 2.0 eq) in DMSO (5.3 mL) was allowed to stir at room temperature for 1 hour. The reaction appeared complete by LCMS. Water was added to the reaction mixture and the resulting precipitate was isolated by suction filtration and washed with water. The precipitate was then triturated with ethyl acetate to afford trans-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl)pyrimidine-2-carbonitrile (21) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.69 (ddd, 1H, J=6.3, 5.1, 1.8 Hz), 7.37-7.18 (m, 3H), 3.85 (s, 3H), 3.03 (ddd, 1H, J=9.3, 4.5, 3.9 Hz), 2.94 (m, 1H), 2.91 (s, 3H), 2.41 (s, 3H), 2.13-1.98 (m, 2H). LRMS m/z (M+H) 371.0 found, 371.2 required. m.p. 229-231° C.

Workup

  1. customthe resulting precipitate was isolated by suction filtration
  2. washwashed with water
  3. customThe precipitate was then triturated with ethyl acetate

Sources & evidence

ORD record
ord-fcd96c9514874edd8db25c934f09a0c8
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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