Cesium carbonate → 2-{[(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]amino}-5-[(1-methyl-1H-pyrazol-4-yl)methyl]-4(1H)-pyrimidinone trifluoroacetate

HRID 706030Notes

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][NH:16][C:17]([NH2:19])=[NH:18])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[C:24]([O-:27])([O-])=[O:25].[Cs+].[Cs+].[OH:30]/[CH:31]=[C:32](/[CH2:37][C:38]1[CH:39]=[N:40][N:41]([CH3:43])[CH:42]=1)\[C:33](OC)=O>CN1C(=O)CCC1>[F:21][C:20]([F:23])([F:22])[C:24]([OH:27])=[O:25].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]3[NH:19][CH:33]=[C:32]([CH2:37][C:38]4[CH:39]=[N:40][N:41]([CH3:43])[CH:42]=4)[C:31](=[O:30])[N:18]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:21])([F:22])[F:23]

Participants

Conditions

Temperature: 130 °C

Procedure

To the mixture of N-[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]guanidine (150 mg, 0.328 mmol) and Cs2CO3 (428 mg, 1.314 mmol) in NMP (1.5 mL) was added methyl (2Z)-3-hydroxy-2-[(1-methyl-1H-pyrazol-4-yl)methyl]-2-propenoate (77 mg, 0.394 mmol). It was heated with a microwave reactor at 130° C. for 1 h. Purification via MDAP then afforded the title compound as a white solid (54 mg, 27.3% yield). LCMS: rt=2.88 min, [M+H+]=490

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-91cee2a0c4fd4f1899cd7d072a49acd8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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