3-(Trifluoromethyl)azetidin-3-ol hydrochloride → [5-Cyclopropyl-6-(cyclopropylmethoxy)pyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone

HRID 625016Notes

Reaction equation

HRID 625016 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.Cl.[F:19][C:20]([F:27])([F:26])[C:21]1([OH:25])[CH2:24][NH:23][CH2:22]1>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([N:23]3[CH2:24][C:21]([OH:25])([C:20]([F:27])([F:26])[F:19])[CH2:22]3)=[O:17])=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 467351523-(Trifluoromethyl)azetidin-3-ol hydrochlorideHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 76281602[5-Cyclopropyl-6-(cyclopropylmethoxy)pyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanoneYield 23%

Procedure

In analogy to the procedure described in Example 127 e), 5-cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 3 c, 20 mg, 85.7 μmol) was reacted with 3-(trifluoromethyl)azetidin-3-ol hydrochloride (CAN 848192-96-1, 18.3 mg, 103 μmol) to obtain the title compound (7 mg, 23%) as colorless oil, MS (EI): m/e=357.3 [MH+].

Sources & evidence

ORD record
ord-5eff8f7bc1bb47ed929fe1196664857f
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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