Diisopropylethylamine → HCID 86648697, compound

HRID 1425225Notes

Reaction equation

HRID 1425225 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH3:20])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].F[C:22]1[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][N:23]=1.C(N(C(C)C)CC)(C)C>>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:22]3[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][N:23]=3)[CH2:15][C@H:14]2[O:19][CH3:20])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 242832HCID 242832, compoundHCID 86648695cis(+/-)-4-Chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648697HCID 86648697, compoundYield 29.2%

Procedure

The same operation as in Example (158a) was performed using cis(±)-4-chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride obtained in Example (159a) (38.22 mg, 0.12 mmol), ethyl 2-fluoropyridine-4-carboxylate (20 mg, 0.12 mmol) (reference: Journal of Medicinal Chemistry; English; 33; 6; 1990; 1667-1675) and diisopropylethylamine (45.85 mg, 0.35 mmol), to obtain 15.3 mg of the title compound as a yellow oily substance (30%).

Sources & evidence

ORD record
ord-545a0d0345d346c591b353457ace632d
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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