Cyanogen Bromide → HCID 178457824, compound

HRID 518741Notes

Reaction equation

HRID 518741 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.O.O.[Sn](Cl)Cl.[NH2:29][C:30]1C=CC(Cl)=CC=1N[C@@H]1CC[C@H](C(NC(C)C)=O)CC1.N#CBr>CCO.C(Cl)Cl>[NH2:29][C:30]1[N:8]([C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:21]=1

Participants

7

Reactant 4

HCID 10476Cyanogen BromideHCID 61436Stannous chloride dihydrateHCID 178457828HCID 178457828, compoundHCID 178457829HCID 178457829, compound

Product 1

HCID 178457824HCID 178457824, compoundYield 124%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of cis-4-(5-chloro-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (2.27 g, 6.68 mmol) in EtOH (66.8 mL) was added tin(II) chloride dihydrate (6.03 g, 26.7 mmol). The reaction was stirred at 80° C. for 90 minutes. The reaction mixture was concentrated, and the residue was partitioned between EtOAc and 1 N aqueous NaOH. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The cis-4-(2-amino-5-chlorophenylamino)-N-isopropylcyclohexanecarboxamide intermediate (2.07 g, 6.68 mmol) was dissolved in EtOH (20 mL), and cyanogen bromide (1.061 g, 10.02 mmol) was added. The reaction was stirred at RT for 1 hour The reaction was diluted with 200 mL DCM and washed with 1 N aqueous NaOH. The organic layer was concentrated to provide cis-4-(2-amino-6-chloro-1H-benzo[d]imidazol-1-yl)-N-isopropylcyclohexanecarboxamide (2.77 g, 124% yield) as a brown oil. MS, m/z (C17H23ClN4O): calcd, 334.2. found, 334.8 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and 1 N aqueous NaOH
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringThe reaction was stirred at RT for 1 hour The reaction
  7. washwashed with 1 N aqueous NaOH
  8. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-cce0f6e387c947aca9788a0524ea0eb1
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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