Piperazin-2-one → (1-{4-[4-oxo-8-(3-oxo-piperazin-1-yl)-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037342Notes

Reaction equation

HRID 1037342 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)[CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)[NH:48]C1(C2C=CC(C3C(=O)C4C(=C(Br)C=CC=4)OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.O=C1CNCCN1>>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([N:29]5[CH2:30][CH2:31][NH:48][C:33](=[O:32])[CH2:34]5)[CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 231360Piperazin-2-oneHCID 67067700{1-[4-(8-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 67067829{1-[4-(8-Morpholin-4-yl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067777(1-{4-[4-oxo-8-(3-oxo-piperazin-1-yl)-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl esterYield 64%

Procedure

Following the procedure of {1-[4-(8-morpholin-4-yl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, {1-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted with 2-oxopiperazine to give the title compound as a white solid (35 mg, 64%). LCMS (Method G): RT=3.45 min, [M+H]+=566.

Sources & evidence

ORD record
ord-0e54e1d35cf64f9a84cbc48f4b6c1a69
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…