9-hydroxy-2-isopropyl-6-[1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl]-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 6-((1-(3,4-Dichlorophenyl)cyclopentyl)methyl)-9-hydroxy-2-isopropyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione

HRID 2169514Notes

Reaction equation

C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[C:33](=[O:34])[C:10]=12)C1C=CC=CC=1.OC1C(=O)N=C(CC2(C3C=CC(C(F)(F)F)=CC=3)CCCC2)N2CCN(C(C)C)C(=O)C=12>>[Cl:29][C:24]1[CH:23]=[C:22]([C:17]2([CH2:16][C:12]3[N:11]4[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[C:33](=[O:34])[C:10]4=[C:9]([OH:8])[C:14](=[O:15])[N:13]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

Reactant 2

HCID 867258889-hydroxy-2-isopropyl-6-[1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl]-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HCID 867261379-(Benzyloxy)-6-((1-(3,4-dichlorophenyl)cyclopentyl)methyl)-2-isopropyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione

Product 1

HCID 867261386-((1-(3,4-Dichlorophenyl)cyclopentyl)methyl)-9-hydroxy-2-isopropyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione

Procedure

6-((1-(3,4-Dichlorophenyl)cyclopentyl)methyl)-9-hydroxy-2-isopropyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (492) was synthesized as a white solid from 9-(benzyloxy)-6-((1-(3,4-dichlorophenyl)cyclopentyl)methyl)-2-isopropyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (491) following the procedure described for 6-[1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl]-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (248).

Sources & evidence

ORD record: ord-5ae838f084bc428ba59989e6390cd3e7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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