4-Phenyl-1-(piperidin-4-yl)-1,3-dihydro-2H-imidazol-2-one → (S)-4-Chloro-7-(2-oxo-2-(4-(2-oxo-4-phenyl-2,3-dihydroimidazol-1-yl)piperidin-1-yl)ethyl)-9-(pyridin-4-ylmethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one

HRID 132485Notes

Reaction equation

Cl.Cl.[Cl:3][C:4]1[C:12]2[NH:11][N:10]=[CH:9][C:8]=2[C:7]2[CH2:13][N:14]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[C:15](=[O:22])[C@H:16]([CH2:18][C:19](O)=[O:20])[CH2:17][C:6]=2[CH:5]=1.[C:30]1([C:36]2[NH:37][C:38](=[O:47])[N:39]([CH:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[CH:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.ClC1C2NN=CC=2C2CN(CC(C)(C)C)C(=O)[C@H](CC(=O)N3CCC(N4CC5C(=CC=CC=5)NC4=O)CC3)CC=2C=1>>[Cl:3][C:4]1[C:12]2[NH:11][N:10]=[CH:9][C:8]=2[C:7]2[CH2:13][N:14]([CH2:23][C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)[C:15](=[O:22])[C@H:16]([CH2:18][C:19](=[O:20])[N:44]3[CH2:43][CH2:42][CH:41]([N:39]4[CH:40]=[C:36]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[NH:37][C:38]4=[O:47])[CH2:46][CH2:45]3)[CH2:17][C:6]=2[CH:5]=1

Participants

Reactant 3

HCID 113455464-Phenyl-1-(piperidin-4-yl)-1,3-dihydro-2H-imidazol-2-one

HCID 11979011(7S)-4-chloro-9-(2,2-dimethylpropyl)-7-[2-oxo-2-[4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidin-1-yl]ethyl]-3,6,7,10-tetrahydropyrazolo[3,4-i][2]benzazepin-8-one

HCID 67202381(S)-2-(4-Chloro-8-oxo-9-(pyridin-4-ylmethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid dihydrochloride

Product 1

HCID 11977525(S)-4-Chloro-7-(2-oxo-2-(4-(2-oxo-4-phenyl-2,3-dihydroimidazol-1-yl)piperidin-1-yl)ethyl)-9-(pyridin-4-ylmethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-oneYield 30%

Procedure

(S)-2-(4-Chloro-8-oxo-9-(pyridin-4-ylmethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid dihydrochloride (100 mg, 0.23 mmol) and 4-phenyl-1-(piperidin-4-yl)-1H-imidazol-2(3H)-one (60 mg, 0.28 mmol) were reacted following a procedure analogous to the preparation of 4-Chloro-9-(2,2-dimethyl-propyl)-7-(S)-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-6,7,9,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-8-one. Title compound was obtained as white solid in 30% yield. MS m/e (M+H)+=610.3. 1H NMR (500 MHz, DMSO-D6): δ=13.46 (s, 1H), 10.68 (d, J=4.27, 1H), 8.30 (d, J=3.97, 2H), 8.23 (s, 1H), 7.50 (d, J=7.93, 1H), 7.45 (d, J=7.63, 1H), 7.31 (m, 2H), 7.22 (s, 1H), 7.14 (m, 4H), 5.41 (d, J=16.78, 1H), 4.66 (m, 3H), 4.55 (m, 1H), 4.13 (m, 2H), 3.99 (m, 1H), 3.33 (m, 1H), 3.18 (m, 1H), 3.05 (dd, J1=16.02, J2=8.70, 1H), 2.94 (m, 1H), 2.68 (m, 1H), 2.44 (m, 1H), 1.81 (m, 3H), 1.62 (m, 1H).

Sources & evidence

ORD record: ord-25f71139007a4aacb61db42b5f504a1d
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384931B2

Reaction notes

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