Cesium carbonate → HCID 178525669, compound

HRID 706027Notes

Reaction equation

HRID 706027 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].[OH:24]/[CH:25]=[C:26](/[CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[N:36][CH:37]=1)\[C:27](OC)=O.[C:38]([O-:41])([O-])=[O:39].[Cs+].[Cs+]>CN1C(=O)CCC1>[F:21][C:20]([F:23])([F:22])[C:38]([OH:41])=[O:39].[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:27]=[C:26]([CH2:31][C:32]4[CH:37]=[N:36][CH:35]=[N:34][CH:33]=4)[C:25](=[O:24])[N:18]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:21])([F:22])[F:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67774726(Z)-methyl 3-hydroxy-2-(pyrimidin-5-ylmethyl)acrylateHCID 178512771HCID 178512771, compound

Product 1

HCID 178525669HCID 178525669, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of N-[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]guanidine (50 mg, 0.109 mmol), methyl (2Z)-3-hydroxy-2-(5-pyrimidinylmethyl)-2-propenoate (33 mg, 0.170 mmol) and Cs2CO3 (143 mg, 0.438 mmol) in NMP (1 mL) was heated with a microwave reactor at 130° C. for 1 h. Purification via MDAP then afforded the title compound (5 mg, 7.60% yield). LCMS: rt=2.93 min, [M+H]=488

Workup

  1. customPurification via MDAP

Sources & evidence

ORD record
ord-cac0ce31b1974b70bbc94bd29cba9217
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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