Benzyl chloroformate → HCID 67265080, compound

HRID 1685155Notes

Reaction equation

HRID 1685155 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][NH:29][CH3:30])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][N:29]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[CH3:30])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 67265091HCID 67265091, compound

Product 1

HCID 67265080HCID 67265080, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-[4-(3-chloro-4-fluoro-phenyl)-1-(2-methylamino-ethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.56 mmol; 680 mg) in DCM (10 mL) and add benzyl chloroformate (1.56 mmol; 0.23 mL) and DIPEA (3.11 mmol; 0.54 mL). Stir 15 min and evaporate. Purify the residue on 120 g silica gel with DCM to 20% EA/DCM to provide the title compound (741 mg; 83%). MS (ES): m/z=571 (M+H).

Workup

  1. customevaporate
  2. customPurify the residue on 120 g silica gel with DCM to 20% EA/DCM

Sources & evidence

ORD record
ord-aad287e5d6a94419a97dd5485be7e503
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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