Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1) → 3-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-(2-morpholinoethyl)-1H-imidazol-2-yl)isophthalate

HRID 529020Notes

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].Cl.Cl[CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]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]([CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[CH:12]=1)=[O:7])[CH2:34][CH2:35][CH3:36]

Participants

Reactant 2

HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

HCID 178449065HCID 178449065, compound

Product 1

HCID 710622953-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-(2-morpholinoethyl)-1H-imidazol-2-yl)isophthalateYield 70%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 274A, 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (280 mg, 0.57 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (106 mg, 0.57 mmol) were converted to the title compound (240 mg, 70%). 1H NMR (CDCl3) δ 8.68 (d, J=1.6 Hz, 1H), 8.23 (dd, J=8.0, 1.6 Hz, 1H), 7.62 (s, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.36-7.32 (m, 3H), 7.25-7.23 (m, 2H), 5.14 (s, 2H), 3.97 (s, 3H), 3.92 (br s, 2H), 3.60-3.54 (m, 6H), 3.45 (br s, 2H), 2.37 (t, J=6.4 Hz, 2H), 2.20-2.18 (m, 4H), 1.63-1.56 (m, 4H), 1.38-1.22 (m, 4H), 0.95-0.82 (m, 6H); MS(ESI+) m/z 605.4 (M+H)+.

Sources & evidence

ORD record: ord-fbd1c643324947d48ca947a624cacf45
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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