HCID 178430407, compound → HCID 178521772, compound

HRID 714347Notes

Reaction equation

CC1CNC(C2C=CN=C(NC(=O)C3C=CC=CC=3)C=2)=N1.[C:22]1([CH:28]2[CH2:32][NH:31][C:30]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][C:40](=[O:47])[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH:34]=3)=[N:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([C:28]2[N:29]=[C:30]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][C:40](=[O:47])[C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[CH:34]=3)[NH:31][CH:32]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Reactant 2

HCID 178430407HCID 178430407, compound

HCID 178521771HCID 178521771, compound

Product 1

HCID 178521772HCID 178521772, compoundYield 13%

Procedure

Following the procedure as described in Example 10, making variations as required to replace N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide with N-(4-(4-phenyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide, N-(4-(4-phenyl-1H-imidazol-2-yl)pyridin-2-yl)benzamide was obtained as a colorless solid in 13% yield: mp 265-267° C.; 1H NMR (300 MHz, DMSO-d6) δ 13.14 (br s, 1H), 10.88 (br s, 1H), 8.81 (s, 1H), 8.47 (d, J=5.2 Hz, 1H), 8.10-8.05 (m, 2H), 7.93-7.88 (m, 2H), 7.72 (dd, J=5.2, 1.5 Hz, 1H), 7.65-7.36 (m, 6H), 7.28-7.21 (m, 1H); 13C NMR (75 MHz, DMSO-d6) δ 165.9, 152.8, 148.5, 143.6, 141.9, 139.1, 134.1, 134.0, 131.9, 128.5, 128.4, 127.9, 126.5, 124.5, 115.8, 115.2, 110.0; MS (ES+) m/z 341.3 (M+1).

Sources & evidence

ORD record: ord-c9876f038e564fff958c0c1b960bc709
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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