5-amino-2H-1,3-benzodiazol-2-one → N-[2,3-dihydro-2-oxo-1H-benzimidazol-5-yl]-2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

반응식

OC1(C2C=CC=CC=2)CCN(C2N=CC([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:19][C:18]=3[C:28]([F:31])([F:30])[F:29])=[O:16])=CC=2)CC1.N[C:39]1[CH:48]=[CH:47][C:42]2=[N:43][C:44](=[O:46])[N:45]=[C:41]2[CH:40]=1.[N+]([C:52]1C=CC2=NC(=O)N=C2C=1)([O-])=O>>[O:46]=[C:44]1[NH:45][C:41]2[CH:40]=[CH:39][C:48]([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH:24]([CH3:52])[CH2:23]4)=[N:19][C:18]=3[C:28]([F:30])([F:31])[F:29])=[O:16])=[CH:47][C:42]=2[NH:43]1

참가 물질

반응물 3

HCID 152505475-amino-2H-1,3-benzodiazol-2-one2회

HCID 227549475-Nitro-2H-benzimidazol-2-one

HCID 46208786N-[6-(4-hydroxy-4-phenylpiperidin-1-yl)pyridin-3-yl]-2-(piperidin-1-yl)-4-(trifluoromethyl)oxazole-5-carboxamide

생성물 1

HCID 67391805N-[2,3-dihydro-2-oxo-1H-benzimidazol-5-yl]-2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

실험 절차

Compound 55 was prepared by the general procedure for compound 1, by using compound A-10 and 5-aminobenzimidazolone as starting materials (5-aminobenzimidazolone was prepared by reduction of 5-nitrobenzimidazolone according to Regan, J. and coll. J. Med. Chem. 2002, 45, 2994-3008). 1H NMR (500 MHz, DMSO-d6) δ 10.67 (s, 1H), 10.60 (s, 1H), 10.01 (s, 1H), 7.42 (s, 1H), 7.17 (br d, 1H, J=8.2 Hz), 6.89 (d, 1H, J=8.5 Hz), 4.10 (m, 2H), 3.04 (br t, 1H, J=12.5 Hz), 2.74 (m, 1H), 1.77 (m, 2H), 1.67 (m, 1H), 1.53 (m, 1H), 1.15 (m, 1H), 0.93 (d, 3H, J=6.6 Hz). MS (M+1): 410.