HCID 178430407, compound → HCID 178439619, compound

HRID 714343Notes

Reaction equation

CC1CNC(C2C=CN=C(NC(=O)C3C=CC=CC=3)C=2)=N1.[CH2:22]([CH:25]1[CH2:29][NH:28][C:27]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([NH:36][C:37](=[O:44])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:31]=2)=[N:26]1)[CH2:23][CH3:24]>>[CH2:22]([C:25]1[N:26]=[C:27]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([NH:36][C:37](=[O:44])[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:31]=2)[NH:28][CH:29]=1)[CH2:23][CH3:24]

Participants

Reactant 2

HCID 178430407HCID 178430407, compound

HCID 178439575HCID 178439575, compound

Product 1

HCID 178439619HCID 178439619, compoundYield 35%

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-propyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide, N-(4-(4-propyl-1H-imidazol-2-yl)pyridin-2-yl)benzamide was obtained as a colorless solid in 35% yield: mp 95-97° C.; 1H NMR (300 MHz, CDCl3) δ 9.16 (br s, 1H), 8.69 (s, 1H), 8.11 (d, J=5.3 Hz, 1H), 7.88-7.82 (m, 2H), 7.70 (dd, J=5.3, 1.4 Hz, 1H), 7.56-7.49 (m, 1H), 7.48-7.37 (m, 2H), 6.87 (s, 1H), 2.54 (t, J=7.4 Hz, 2H), 1.69-1.55 (m, 2H), 0.90 (t, J=7.4 Hz, 3H); MS (ES+) m/z 307.3 (M+1).

Sources & evidence

ORD record: ord-dc014a1b52664269b34d70c182fde590
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

Loading…