Cesium carbonate → HCID 71186482, compound

HRID 712865Notes

Reaction equation

HRID 712865 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1C=[CH:32][C:6]([CH2:7][N:8]2[CH2:15][CH2:14][C:11]3([CH2:13][CH2:12]3)[CH2:10][CH:9]2[C:16]([NH:18][C:19]2([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=3)[CH2:21][CH2:20]2)=[O:17])=[CH:5][CH:4]=1.ClCC1C=[N:40]C(C(F)(F)F)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[F:35][C:2]([F:1])([F:34])[C:3]1[N:40]=[CH:32][C:6]([CH2:7][N:8]2[CH2:15][CH2:14][C:11]3([CH2:13][CH2:12]3)[CH2:10][CH:9]2[C:16]([NH:18][C:19]2([C:22]3[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=3)[CH2:20][CH2:21]2)=[O:17])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 71186594HCID 71186594, compound

Product 1

HCID 71186482HCID 71186482, compoundYield 93.8%

Procedure

The title compound (D124) (47 mg) was prepared according to the general procedure for substituted benzyl amines preparation starting from methyl 4-(1-(6-(4-(trifluoromethyl)benzyl)-6-azaspiro[2.5]octane-5-carboxamido)cyclopropyl)benzoate (D90) (50 mg) and 3-chloromethyl-6-(trifluoromethyl)piridine (38 mg). (Cs2CO3: 1.3 eq; reaction time: 18 hrs; RT)

Sources & evidence

ORD record
ord-67169936f6354f3395f222c164baa19b
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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