HCID 178488056, compound → HCID 178519407, compound

HRID 1913160Notes

Reaction equation

HRID 1913160 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[NH:19][C:18]4[CH:20]=[CH:21][C:22]([O:24]C)=[CH:23][C:17]=4[N:16]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:3][CH:2]=1>C(Cl)Cl>[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[NH:19][C:18]4[CH:20]=[CH:21][C:22]([OH:24])=[CH:23][C:17]=4[N:16]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 178488056HCID 178488056, compound

Product 1

HCID 178519407HCID 178519407, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of biphenyl-4-yl[4-(5-methoxy-1H-benzimidazol-2-yl)piperidin-1-yl]methanone (40 mg, 0.097 mmol) in DCM (1 mL) at −60° C. is added BBr (14 μL). After 30 mins the reaction mixture is warmed to room temperature, diluted with DCM and washed with water. The organic layer is concentrated under reduced pressure. Purification by preparative HPLC gives 6 mg of biphenyl-4-yl[4-(5-hydroxy-1H-benzimidazol-2-yl)piperidin-1-yl]methanone.

Workup

  1. washwashed with water
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-64bac7b7cc7b47ddb9e5cf582e56702c
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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