5-amino-2H-1,3-benzodiazol-2-one → HCID 67391805, compound

HRID 1020375Notes

Reaction equation

HRID 1020375 reaction equation
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

Participants

4

Reactant 3

HCID 152505475-amino-2H-1,3-benzodiazol-2-one2×HCID 227549475-Nitro-2H-benzimidazol-2-oneHCID 46208786HCID 46208786, compound

Product 1

HCID 67391805HCID 67391805, compound

Procedure

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.

Sources & evidence

ORD record
ord-194778d198c14f64aa59eb7db2f2f504
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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