3-(1H-imidazol-2-yl)propan-1-ol → 2-Fluoro-4-[3-(fur-2-yl)carbamoyloxypropyl]-1-triphenylmethylimidazole

HRID 2412479Notes

Reaction equation

HRID 2412479 reaction equation
O[CH2:2][CH2:3]CC1NC=CN=1.[C:10]([NH:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][C:20]1[N:21]=[C:22]([F:44])[N:23]([C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=1)=[O:15])(=[O:12])[CH3:11]>>[F:44][C:22]1[N:23]([C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[C:20]([CH2:19][CH2:18][CH2:17][O:16][C:14](=[O:15])[NH:13][C:10]2[O:12][CH:2]=[CH:3][CH:11]=2)[N:21]=1

Participants

3

Reactant 2

HCID 179252873-(1H-imidazol-2-yl)propan-1-olHCID 204324074-(3-Acetylcarbamoyloxypropyl)-2-fluoro-1-triphenylmethylimidazole

Product 1

HCID 204323942-Fluoro-4-[3-(fur-2-yl)carbamoyloxypropyl]-1-triphenylmethylimidazole

Procedure

A suspension of 2-furoamide in 1,2-dichloroethane was treated with oxalyl chloride; 2-furoylisocyanate was isolated by distillation. This product was reacted with the hydroxypropylimidazole, as for the starting material of Example 12, to give 2-fluoro-4-[3-(fur-2-yl)carbamoyloxypropyl]-1-triphenylmethylimidazole, having the following n.m.r. spectrum in d6DMSO: 1.82 (m, 2H); 2.47 (t, 2H); 4.07 (t, 2H); 6.3 (s, 1H); 6.64 (m, 1H); 7.0-7.45 (m, 15H); 7.5 (m, 1H); 7.91 (m, 1H); 10.1 (br, 1H).

Sources & evidence

ORD record
ord-2e043327950e442eb5b50a35644ffebe
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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