(3-Bromopropyl)benzene → 3-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-(3-phenylpropyl)-1H-imidazol-2-yl)isophthalate

HRID 529013Notes

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].Br[CH2:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH2:33]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[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:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[N:11]([CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:12]=1)=[O:7])[CH2:34][CH2:35][CH3:36]

Participants

Reactant 2

HCID 12503(3-Bromopropyl)benzene

HCID 178449065HCID 178449065, compound

Product 1

HCID 710624223-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-(3-phenylpropyl)-1H-imidazol-2-yl)isophthalateYield 76.7%

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, 0.4 mmol) and (3-bromopropyl)benzene (97 mg, 0.48 mmol) were converted the title compound (187 mg, 74%). 1H NMR (CDCl3) 8.65 (d, J=1.6 Hz, 1H), 8.20 (dd, J=8.0, 1.6 Hz, 1H), 7.53 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.33-7.30 (m, 4H), 7.24-7.14 (m, 4H), 6.94 (d, J=8.0 Hz, 2H), 5.13 (s, 2H), 4.00 (s, 3H), 3.99 (br s, 2H), 3.52 (t, J=7.6 Hz, 2H), 3.46 (br s, 2H), 2.39 (t, J=7.6 Hz, 2H), 1.82-1.78 (m, 2H), 1.55-1.50 (m, 4H), 1.26-1.22 (m, 4H), 0.96-0.83 (m, 6H); MS(ESI+) m/z 610.2 (M+H)+.

Sources & evidence

ORD record: ord-cbe677ef37034759a733365acef7d379
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

Loading…