(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 → N-((R)-9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)-4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxamide

HRID 132273Notes

Reaction equation

HRID 132273 reaction equation
[CH2:1]([N:8]1[C:21](=[O:22])[C@H:20](CC(O)=O)[CH2:19][C:18]2[CH:17]=[CH:16][C:15]3[NH:14][N:13]=[CH:12][C:11]=3[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][CH:30]([CH:33]2[CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]2=[O:43])[CH2:29][CH2:28]1.ClC1C2NN=CC=2C2CN(CC(C)(C)C)C(=O)[C@H](CC(=O)N3CCC([N:67]4CC5C(=CC=CC=5)N[C:68]4=[O:77])CC3)CC=2C=1>>[CH2:1]([N:8]1[C:21](=[O:22])[C@H:20]([NH:67][C:68]([N:27]2[CH2:28][CH2:29][CH:30]([CH:33]3[CH2:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[NH:35][C:34]3=[O:43])[CH2:31][CH2:32]2)=[O:77])[CH2:19][C:18]2[CH:17]=[CH:16][C:15]3[NH:14][N:13]=[CH:12][C:11]=3[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

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-oneHCID 183212463-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 59731963(S)-2-(9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid

Product 1

HCID 11979017N-((R)-9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)-4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxamideYield 33%

Procedure

(S)-2-(9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid (80 mg, 0.24 mmol) and 3-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (75 mg, 0.33 mmol) were reacted in a manner 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. Material was obtained as white solid in 33% yield. MS m/e (M+H)+=542.3. 1H NMR (500 MHz, DMSO-D6): δ=13.01 (s, 1H), 10.11 (s, 1H), 8.21 (s, 1H), 7.36 (d, J=7.93, 1H), 7.17 (m, 1H), 7.11 (m, 2H), 6.91 (m, 1H), 6.83 (d, J=7.63, 1H), 5.35 (d, J=17.09, 1H), 4.61 (d, J=17.40, 1H), 4.38 (m, 1H), 4.02 (m, 1H), 3.83 (s, 1H), 3.55 (t, J=12.36, 1H), 2.95 (m, 6H), 2.79 (m, 1H), 2.42 (m, 1H), 2.31 (m, 2H), 1.90 (m, 1H), 1.63 (m, 2H), 1.17 (m, 1H), 0.72 (d, J=9.77, 9H).

Workup

  1. customMaterial was obtained as white solid in 33% yield

Sources & evidence

ORD record
ord-846e370d95c24d658b5377c2540c5867
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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