HCID 178430407, compound → HCID 178441348, compound

HRID 714345Notes

Reaction equation

CC1CNC(C2C=CN=C(NC(=O)C3C=CC=CC=3)C=2)=N1.[CH2:22]([CH:26]1[CH2:30][NH:29][C:28]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:38](=[O:45])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:32]=2)=[N:27]1)[CH:23]([CH3:25])[CH3:24]>>[CH2:22]([C:26]1[N:27]=[C:28]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:38](=[O:45])[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:32]=2)[NH:29][CH:30]=1)[CH:23]([CH3:25])[CH3:24]

Participants

Reactant 2

HCID 178430407HCID 178430407, compound

HCID 178441250HCID 178441250, compound

Product 1

HCID 178441348HCID 178441348, compoundYield 36%

Procedure

Following the procedure as described in Example 10, making non-critical variations as required to replace N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide with N-(4-(4-isobutyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide, N-(4-(4-isobutyl-1H-imidazol-2-yl)pyridin-2-yl)benzamide was obtained as a colorless solid in 36% yield: mp 103-105° C.; 1H NMR (300 MHz, CDCl3) δ 9.07 (br s, 1H), 8.68 (s, 1H), 8.17 (d, J=5.2 Hz, 1H), 7.86 (d, J=7.3 Hz, 2H), 7.73 (d, J=5.3 Hz, 1H), 7.59-7.40 (m, 3H), 6.89 (s, 1H), 2.45 (d, J=7.1 Hz, 2H), 1.98-1.79 (m, 1H), 0.90 (d, J=6.6 Hz, 6H); MS (ES+) m/z 321.3 (M+1).

Sources & evidence

ORD record: ord-703ad514a1fd448191322d684e0723b7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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