Hydrogen Bromide → 5-cyclopropyl-4-(2,2-difluoroethoxy)-N-(2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(methylsulfonyl)propan-2-yl)picolinamide

HRID 1480337Notes

Reaction equation

HRID 1480337 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][CH:15]([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.Cl.[CH3:19][C:20]1[O:24][N:23]=[C:22]([C:25]([NH2:32])([CH3:31])[CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[N:21]=1.Br>>[CH:1]1([C:4]2[C:5]([O:13][CH2:14][CH:15]([F:17])[F:16])=[CH:6][C:7]([C:10]([NH:32][C:25]([C:22]3[N:21]=[C:20]([CH3:19])[O:24][N:23]=3)([CH3:31])[CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])=[O:12])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineHCID 902035305-Cyclopropyl-4-(2,2-difluoroethoxy)pyridine-2-carboxylic acid

Product 1

HCID 902040925-cyclopropyl-4-(2,2-difluoroethoxy)-N-(2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(methylsulfonyl)propan-2-yl)picolinamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-cyclopropyl-4-(2,2-difluoroethoxy)pyridine-2-carboxylic acid;hydrochloride (example 145d) and 2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine;hydrobromide (enantiomer B) (example 125b) as starting materials and isolated (25 mg, 31%); MS (ESI, m/z): 445.3 (M+H+).

Workup

  1. customisolated (25 mg, 31%)

Sources & evidence

ORD record
ord-6c1cf3c870274a6bb99b8513efb5ca68
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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