Cyanogen Bromide → HCID 178491277, compound

HRID 518676Notes

Reaction equation

HRID 518676 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[NH:18][C@@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]([NH:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.[N:31]#[C:32]Br>CCO>[NH2:31][C:32]1[N:18]([C@@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([NH:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:3]2[CH:4]=[C:5]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 178491294HCID 178491294, compound

Product 1

HCID 178491277HCID 178491277, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of cis-4-(2-amino-5-(4-methoxybenzyloxy)phenylamino)-N-isopropylcyclohexanecarboxamide (400 mg, 0.972 mmol) in EtOH (4.8 mL) was added cyanic bromide (165 mg, 1.555 mmol) and the mixture was stirred at RT for 2 hours. The solvent was evaporated, and the residue was diluted with DCM (about 10 mL), washed with water, 1N aqueous NaOH, and brine. The organic layer was dried over Na2SO4, filtered and the solvent was removed to afford cis-4-(2-amino-6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-1-yl)-N-isopropylcyclohexanecarboxamide (424 mg).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with DCM (about 10 mL)
  3. washwashed with water, 1N aqueous NaOH, and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-87cabf17fad04992a1b5bbb6d5effb5f
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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