((S)-4-Bromo-9-cyclopropylmethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohept[e]inden-7-yl)-acetic acid → (S)-4-bromo-9-(cyclopropylmethyl)-7-(2-(4-(8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)piperidin-1-yl)-2-oxoethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one

HRID 132283Notes

Reaction equation

HRID 132283 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:12]([CH2:21][CH:22]3[CH2:24][CH2:23]3)[C:13](=[O:20])[C@H:14]([CH2:16][C:17]([OH:19])=O)[CH2:15][C:4]=2[CH:3]=1.Cl.[F:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[NH:35][C:34](=[O:37])[C:33]([CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[CH:32]2.ClC1C2NN=CC=2C2CN(CC(C)(C)C)C(=O)[C@@H](CC(=O)N3CCC(N4CC5C(=CC=CC=5)NC4=O)CC3)CC=2C=1>>[Br:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:12]([CH2:21][CH:22]3[CH2:24][CH2:23]3)[C:13](=[O:20])[C@H:14]([CH2:16][C:17]([N:41]3[CH2:42][CH2:43][CH:38]([C:33]4[C:34](=[O:37])[NH:35][C:36]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][C:27]=5[F:26])[CH2:39][CH2:40]3)=[O:19])[CH2:15][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 59731996((S)-4-Bromo-9-cyclopropylmethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohept[e]inden-7-yl)-acetic acidHCID 673189488-Fluoro-3-(piperidin-4-yl)quinolin-2(1H)-one hydrochlorideHCID 688264794-Chloro-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

Product 1

HCID 11978658(S)-4-bromo-9-(cyclopropylmethyl)-7-(2-(4-(8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)piperidin-1-yl)-2-oxoethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-oneYield 56%

Procedure

((S)-4-Bromo-9-cyclopropylmethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohept[e]inden-7-yl)-acetic acid (90 mg, 0.23 mmol) and 8-fluoro-3-(piperidin-4-yl)quinolin-2(1H)-one hydrochloride (80 mg, 0.28 mmol) were combined in a manner analogous to the preparation of 4-Chloro-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. Title compound was obtained as white solid in 56% yield. High resolution MS m/e (M+H)+=620.1665.

Sources & evidence

ORD record
ord-c873af2f64294812832fa45872f8d3a3
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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