9-(2,2-Dimethyl-propyl)-7-(R)-{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 → (S)-9-Neopentyl-7-(2-oxo-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidin-1-yl)ethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one

HRID 1985547Notes

Reaction equation

HRID 1985547 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:9](=[O:18])[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:4][CH2:3]1.[CH3:19][C:20]([CH3:58])([CH3:57])[CH2:21][N:22]1[CH2:35][C:27]2[C:28]3[CH:29]=[N:30][NH:31][C:32]=3[CH:33]=[CH:34][C:26]=2[CH2:25][C@H:24]([CH2:36][C:37](=[O:55])N2CCC(N3CC4C(=CC=CC=4)NC3=O)CC2)[C:23]1=[O:56]>>[CH2:21]([N:22]1[C:23](=[O:56])[C@H:24]([CH2:36][C:37](=[O:55])[N:2]2[CH2:3][CH2:4][CH:5]([C:8]3[C:9](=[O:18])[NH:10][C:11]4[C:16]([CH:17]=3)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:6][CH2:7]2)[CH2:25][C:26]2[CH:34]=[CH:33][C:32]3[NH:31][N:30]=[CH:29][C:28]=3[C:27]=2[CH2:35]1)[C:20]([CH3:58])([CH3:57])[CH3:19]

Participants

3

Reactant 2

HCID 597319619-(2,2-Dimethyl-propyl)-7-(R)-{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-oneHCID 673176623-piperidin-4-yl-1H-quinolin-2-one;hydrochloride

Product 1

HCID 59732040(S)-9-Neopentyl-7-(2-oxo-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidin-1-yl)ethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-oneYield 31%

Procedure

Title compound was prepared from 3-(piperidin-4-yl)quinolin-2(1H)-one hydrochloride in a manner analogous to the preparation of 9-(2,2-Dimethyl-propyl)-7-(R)-{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 31% yield. MS m/e (M+H)+=540.2. 1H NMR (500 MHz, DMSO-D6): δ=11.76 (s, 1H), 8.22 (s, 1H), 7.70 (d, J=8.85, 1H), 7.62 (s, 1H), 7.43 (t, J=7.48, 1H), 7.37 (d, J=8.55, 1H), 7.28 (d, J=8.24, 1H), 7.15 (t, J=7.32, 1H) 7.11 (d, J=8.55, 1H), 5.38 (d, J=17.09, 1H), 4.62 (d, J=16.79, 1H), 4.55 (d, J=11.29, 1H), 4.13 (s, 1H), 3.88 (s, 1H), 3.58 (s, 2H), 3.16 (m, 2H), 3.07 (m, 3H), 2.88 (t, J=14.34, 1H), 2.64 (m, 1H), 2.36 (m, 1H), 1.92 (d, J=10.38, 1H), 1.84 (d, J=11.29, 1H), 1.57 (m, 1H), 1.40 (m, 1H), 0.73 (s, 9H).

Workup

  1. customMaterial was obtained as white solid in 31% yield

Sources & evidence

ORD record
ord-d4feb4e4fa2c46339b0f2f6f9310a14d
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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