Acetonitrile → HCID 117899599, compound

HRID 522294Notes

Reaction equation

FC(F)(F)C(O)=O.[C:8]([C:10]1[N:18]=[C:17]2[C:13]([N:14]=[C:15]([CH3:20])[N:16]2[CH3:19])=[C:12]([C:21]2[CH:42]=[CH:41][C:24]([O:25][CH2:26][CH2:27][CH:28]3[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]3)=[C:23]([C:43]([F:46])([F:45])[F:44])[CH:22]=2)[N:11]=1)#[N:9].C(#N)C.C(Cl)[Cl:51]>>[ClH:51].[CH3:20][C:15]1[N:16]([CH3:19])[C:17]2[C:13]([N:14]=1)=[C:12]([C:21]1[CH:42]=[CH:41][C:24]([O:25][CH2:26][CH2:27][CH:28]3[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]3)=[C:23]([C:43]([F:45])([F:46])[F:44])[CH:22]=1)[N:11]=[C:10]([C:8]#[N:9])[N:18]=2

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 117899603HCID 117899603, compound

Product 1

HCID 117899599HCID 117899599, compound

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of tert-butyl 4-{2-[4-(2-cyano-8,9-dimethyl-9H-purin-6-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylate (100 mg) in CH2Cl2 (2 mL)-acetonitrile (0.5 mL) at room temperature, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and CH2Cl2 (2 mL) was added to the residue. A 4 M solution of hydrogen chloride in EtOAc (0.2 mL) was added to the mixture at room temperature, and the precipitate was collected by filtration, whereby 8,9-dimethyl-6-{4-[2-(piperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-9H-purine-2-carbonitrile monohydrochloride (59 mg) was obtained as a white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, and CH2Cl2 (2 mL)
additionwas added to the residue
additionA 4 M solution of hydrogen chloride in EtOAc (0.2 mL) was added to the mixture at room temperature
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-2d94a6c13ef44639b4f8ef4546fd16c8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328118B2

Reaction notes

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