Cyanogen Bromide → HCID 178457825, compound

HRID 518739Notes

Reaction equation

HRID 518739 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:14][C@@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.[N:27]#[C:28]Br>CCO.C(Cl)Cl>[NH2:27][C:28]1[N:14]([C@@H:15]2[CH2:16][CH2:17][C@H:18]([C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)[C:3]2[CH:4]=[C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 178457842HCID 178457842, compound

Product 1

HCID 178457825HCID 178457825, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The cis-4-(2-amino-5-morpholinophenylamino)-N-isopropylcyclohexanecarboxamide (315 mg, 0.874 mmol) was dissolved in EtOH (5 mL), and cyanogen bromide (139 mg, 1.311 mmol) was added. The reaction was stirred at RT. After 16 hours, the reaction was diluted with DCM (50 mL) and washed with 1 N aqueous NaOH. The organic layer was concentrated to provide cis-4-(2-amino-6-morpholino-1H-benzo[d]imidazol-1-yl)-N-isopropylcyclohexanecarboxamide as a light purple solid (210 mg, 62.3% yield). MS, m/z (C21H31N5O2): calcd, 385.2. found, 385.8 [M+H].

Workup

  1. washwashed with 1 N aqueous NaOH
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-995a1d793f3d4b1c8475c2131aa9958b
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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