Acetic Acid → benzyl {2-(4-bromophenyl)-1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]ethyl}carbamate

HRID 425390Notes

Reaction equation

[CH3:1][NH2:2].C(O)(=O)C.[Br:7][C:8]1[CH:38]=[CH:37][C:11]([CH2:12][CH:13]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:14]([NH:16][CH2:17][C:18](=O)[CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][CH3:22])=O)=[CH:10][CH:9]=1>C1(C)C(C)=CC=CC=1>[Br:7][C:8]1[CH:38]=[CH:37][C:11]([CH2:12][CH:13]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:14]2[N:2]([CH3:1])[C:18]([CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][CH3:22])=[CH:17][N:16]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Methylamine (2 M in tetrahydrofuran) (1.2 mL, 24 mmol) followed by acetic acid (1.2 mL) were added to an ambient temperature solution of benzyl {1-(4-bromobenzyl)-2-[(4,4-dimethyl-2-oxohexyl)amino]-2-oxoethyl}carbamate (for synthesis see Example 37) (600 mg, 1.2 mmol) in xylene (10 mL). After stirring at 150° C. for 2 h, the reaction mixture was concentrated in vacuo. High pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid afforded benzyl {2-(4-bromophenyl)-1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]ethyl}carbamate.

Workup

concentrationthe reaction mixture was concentrated in vacuo
washHigh pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid

Sources & evidence

ORD record: ord-1045dd39d2d64d278a95f56615598d0c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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