Benzyl Bromide → 3-Benzyl 1-methyl 4-(1-benzyl-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate

HRID 529014Notes

Reaction equation

[CH2:1]([N:5]([CH2:33][CH2:34][CH2:35][CH3:36])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[NH:11][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH2:37]([N:11]1[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:33][CH2:34][CH2:35][CH3:36])[N:9]=[C:10]1[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 178449065HCID 178449065, compound

Product 1

HCID 867189343-Benzyl 1-methyl 4-(1-benzyl-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalateYield 77.4%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 271F, 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (200 mg, 0.40 mmol) and benzylbromide (83 mg, 0.48 mmol) were converted to the title compound (180 mg, 76%). 1H NMR (CDCl3) 8.68 (d, J=1.6 Hz, 1H), 8.15 (dd, J=8.0, 2.0 Hz, 1H), 7.43 (s, 1H), 7.39-7.34 (m, 4H), 7.28-7.26 (m, 2H), 7.21-7.17 (m, 3H), 6.90-6.88 (m, 2H), 5.15 (s, 2H), 4.64 (s, 2H), 3.96 (s, 3H), 3.90 (br s, 2H), 3.43 (br s, 2H), 1.70-1.59 (m, 4H), 1.37-1.23 (m, 4H), 0.93-0.82 (m, 6H); MS(ESI+) m/z 582.2 (M+H)+.

Sources & evidence

ORD record: ord-75b72ddaeebf47b898db43ec111509af
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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