N-bromobutanimide → HCID 178461197, compound

HRID 81107Notes

Reaction equation

HRID 81107 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:21]3[N:22]([CH2:25][C@H:26]4[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]4)[CH:23]=[N:24][C:20]=3[CH:19]=[C:18]([C:33]#[N:34])[N:17]=2)[CH:13]=[N:14][CH:15]=1>C(Cl)(Cl)Cl.ClCCl>[Br:1][C:23]1[N:22]([CH2:25][C@H:26]2[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]2)[C:21]2[C:16]([C:12]3[CH:13]=[N:14][CH:15]=[C:10]([Cl:9])[CH:11]=3)=[N:17][C:18]([C:33]#[N:34])=[CH:19][C:20]=2[N:24]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178461253HCID 178461253, compound

Product 1

HCID 178461197HCID 178461197, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

N-bromosuccinimide (5.84 g, 32.8 mmol) was added to a room temperature solution of 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (4 g, 10.9 mmol) stirring in degassed chloroform (54.7 mL). The reaction was heated to reflux for 1 hour. The mixture was cooled to room temperature, diluted with dichloromethane, and washed with saturated aqueous sodium thiosulfate (2×) and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford 2-bromo-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd. for C20H19BrClN5 [M+H]+ 444. found 444. 1H NMR (500 MHz, DMSO-d6) δ 8.87 (s, 1H), 8.84 (s, 1H), 8.57 (s, 1H), 8.40 (s, 1H), 3.86 (d, J=6.1, 2H), 1.44 (d, J=12.1, 2H), 1.15-1.05 (broad, 1H), 1.00-0.85 (broad, 1H), 0.85-0.73 (m, 4H), 0.72 (d, J=6.1, 3H), 0.56-0.43 (m 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. washwashed with saturated aqueous sodium thiosulfate (2×) and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-c5505fbecd4c459b924f3dd1cd7ef000
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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