Piperazine → HCID 178518546, compound

HRID 474809Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24]O)[C:21](=[O:23])[N:22]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].CC(OC(/N=N/C(O[CH:41]([CH3:43])[CH3:42])=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:63]1CCN[CH2:65][CH2:64]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24][N:63]4[CH2:42][CH2:41][CH2:43][CH2:65][CH2:64]4)[C:21](=[O:23])[N:22]=3)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:26]([F:27])([F:28])[F:29]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-{[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]thio}-5-(hydroxymethyl)-4(1H)-pyrimidinone (51 mg, 0.115 mmol) in dry DMF (3 mL) was added DIAD (0.034 mL, 0.173 mmol), triphenylphosphine (45.3 mg, 0.173 mmol) and piperizine (19.61 mg, 0.230 mmol) under argon. The mixture was heated with a microwave reactor at 45° C. for 0.5 h. Purification via MDAP then afforded the title compound (28 mg, 47.7% yield). LCMS: rt=3.02 min, [M+H+]=510

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-38228156f6914af292d9f831f8ece132
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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