HCID 178430407, compound → HCID 178521776, compound

HRID 714346Notes

Reaction equation

CC1CNC(C2C=CN=C(NC(=O)C3C=CC=CC=3)C=2)=N1.[F:22][C:23]1[CH:24]=[C:25]([CH:47]=[C:48]([F:50])[CH:49]=1)[CH2:26][CH:27]1[CH2:31][NH:30][C:29]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([NH:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:33]=2)=[N:28]1>>[F:50][C:48]1[CH:47]=[C:25]([CH:24]=[C:23]([F:22])[CH:49]=1)[CH2:26][C:27]1[N:28]=[C:29]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([NH:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:33]=2)[NH:30][CH:31]=1

Participants

Reactant 2

HCID 178430407HCID 178430407, compound

HCID 178521775HCID 178521775, compound

Product 1

HCID 178521776HCID 178521776, compoundYield 32%

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-(3,5-difluorobenzyl)-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide, N-(4-(4-(3,5-difluorobenzyl)-1H-imidazol-2-yl)pyridin-2-yl)benzamide was obtained as a colorless solid in 32% yield: 1H NMR (300 MHz, CDCl3) δ 8.98 (br s, 1H), 8.67 (s, 1H), 8.22 (d, J=3.6 Hz, 1H), 7.88-7.81 (m, 2H), 7.73 (d, J=4.8 Hz, 1H), 7.61-7.40 (m, 3H), 6.82 (s, 1H), 6.78-6.70 (m, 1H), 6.66-6.57 (m, 2H), 3.94 (s, 2H); MS (ES+) m/z 391.1 (M+1).

Sources & evidence

ORD record: ord-2b85805d4e3b42b1baf1598681b8bc5d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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