1-Cyclohexyl-2-imidazolidinone → 3-Cyclohexyl-N-(3-fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-oxoimidazolidine-1-carboxamide

HRID 2193753Notes

Reaction equation

HRID 2193753 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:25]([N:27]2[CH2:31][CH2:30][N:29](N3CCCCC3)[C:28]2=[O:38])=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]=[CH:20][N:21]([CH3:23])[CH:22]=3)[S:17][C:10]=12.[CH:39]1(N2CCNC2=O)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>>[CH:39]1([N:29]2[CH2:30][CH2:31][N:27]([C:25]([NH:24][C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]4[CH:14]=[CH:13][N:12]=[C:11]5[CH:15]=[C:16]([C:18]6[N:19]=[CH:20][N:21]([CH3:23])[CH:22]=6)[S:17][C:10]=45)=[C:2]([F:1])[CH:3]=3)=[O:26])[C:28]2=[O:38])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 5803521-Cyclohexyl-2-imidazolidinoneHCID 58790362N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-oxo-3-(piperidin-1-yl)imidazolidine-1-carboxamide

Product 1

HCID 587900743-Cyclohexyl-N-(3-fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-oxoimidazolidine-1-carboxamideYield 68%

Procedure

Following the procedure described above for the compound 276 (example 113) but replacing 1-(piperidin-1-yl)imidazolidin-2-one (278) by 1-cyclohexylimidazolidin-2-one (281), the title compound 279 was obtained in 68% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.69 (s, 1H), 8.44 (dd, J=5.5 Hz, 1H), 7.86 (s, 1H), 7.79 (dd, J=2.5 Hz, J=13 Hz, 1H), 7.72 (s, 1H), 7.68 (s, 1H), 7.46 (t, J=8.9 Hz, 1H), 7.35 (d, J=5.5 Hz, 1H), 6.58 (d, J=5.5 Hz, 1H), 3.8 (dd, J=7.6 Hz, J=8.0 Hz, 2H), 3.73 (s, 3H), 3.7-3.6 (m, 1H), 3.44 (dd, J=7.2 Hz, J=8.0 Hz, 2H), 1.79-1.60 (m, 5H), 1.47-1.41 (m, 2H), 1.36-1.29 (m, 2H), 1.7 (m, 1H). MS (m/z): (M+1) 535.2.

Sources & evidence

ORD record
ord-a457062c93ec4883b1fc1d5d2c3b8517
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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