N-bromobutanimide → (R)-7-bromo-4-((1-cyclobutylethyl)amino)-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile

HRID 1852691Notes

Reaction equation

HRID 1852691 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH:9]1([C@H:13]([NH:15][C:16]2[C:21]3[N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)[CH:23]=[N:24][C:20]=3[CH:19]=[C:18]([C:36]#[N:37])[N:17]=2)[CH3:14])[CH2:12][CH2:11][CH2:10]1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:8][C:19]1[C:20]2[N:24]=[CH:23][N:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=3)[C:21]=2[C:16]([NH:15][C@@H:13]([CH:9]2[CH2:12][CH2:11][CH2:10]2)[CH3:14])=[N:17][C:18]=1[C:36]#[N:37]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86724463(R)-4-((1-cyclobutylethyl)amino)-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile

Product 1

HCID 86724462(R)-7-bromo-4-((1-cyclobutylethyl)amino)-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

NBS (73.5 mg, 0.413 mmol) was added to a stirred, room temperature mixture of (R)-4-((1-cyclobutylethyl)amino)-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (150 mg, 0.376 mmol) in degassed chloroform (3 ml) in a sealed tube. The mixture was heated to 45° C. and stirred under Ar for 1 hour. The mixture was cooled to room temperature and diluted with DCM. The mixture was then transferred to a separatory funnel, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting dark orange oil was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford (R)-7-bromo-4-((1-cyclobutylethyl)amino)-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd for C21H19BrF3N5 [M+H]+ 479. found 479.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe mixture was then transferred to a separatory funnel
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting dark orange oil was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-eb8001878f334079b14558fd31de4630
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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