3-Methylazetidine hydrochloride → {3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(3-methyl-azetidin-1-yl)methanone

HRID 1642980Notes

Reaction equation

HRID 1642980 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([CH:9]3[CH2:14][CH:13]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=4)[CH2:12][N:11]([C:25]([O:27]C4C=CC([N+]([O-])=O)=CC=4)=O)[CH2:10]3)[O:6][N:5]=2)[CH2:3][CH2:2]1.Cl.[CH3:38][CH:39]1[CH2:42][NH:41][CH2:40]1>>[CH:1]1([C:4]2[N:8]=[C:7]([CH:9]3[CH2:14][CH:13]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=4)[CH2:12][N:11]([C:25]([N:41]4[CH2:42][CH:39]([CH3:38])[CH2:40]4)=[O:27])[CH2:10]3)[O:6][N:5]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 251591883-Methylazetidine hydrochlorideHCID 580021744-Nitrophenyl 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 58002596{3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(3-methyl-azetidin-1-yl)methanone

Procedure

95 mg (0.19 mmol) of the compound from Example 184A and 61 mg (0.57 mmol) of 3-methylazetidine hydrochloride were reacted according to the General Method 6. Work-up of the crude product was carried out initially by column chromatography on silica gel (mobile phase: dichloromethane->dichloromethane/methanol 100:5) and additionally by preparative HPLC. Yield: 14 mg (17% of theory)

Sources & evidence

ORD record
ord-a6dc42a042064022981a8d0e002db929
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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