Isobutyryl chloride → [5-(Benzyl-isobutyryl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

HRID 15580

Reaction equation

HRID 15580 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:7]([O:11][C:12](=[O:34])[CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:31][CH2:32][CH3:33])([CH3:10])([CH3:9])[CH3:8].CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.Cl>[C:7]([O:11][C:12](=[O:34])[CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][C:21]([N:23]([CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:31][CH2:32][CH3:33])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 67200053(5-Benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 67200174[5-(Benzyl-isobutyryl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (38 μL, 0.36 mmol) was added to a solution of (5-benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester (45 mg, 0.12 mmol), DIEA (41 μL, 0.24 mmol) and DMAP (15 mg, 0.12 mmol) in CH2Cl2 (1 mL), and stirred overnight at room temperature. The reaction solution was diluted with aqueous HCl (1.0 M) and filtered through an Extrelut column. The Extrelut column was washed with CH2Cl2, and the filtrate was concentrated to afford the subtitle compound that was used without further purification. MS calculated for C27H35N3O3+H: 450, observed: 450.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe Extrelut column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6214346e4a9842cb87e4219a874af32a
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Linked notes

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