Hydrogen Bromide → 5-cyclopropyl-4-(2-fluoroethoxy)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]pyridine-2-carboxamide

HRID 1480331Notes

Reaction equation

HRID 1480331 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][CH2:15][F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[CH3:17][C:18]1[O:22][N:21]=[C:20]([C:23]([NH2:30])([CH3:29])[CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])[N:19]=1.Br>>[CH:1]1([C:4]2[C:5]([O:13][CH2:14][CH2:15][F:16])=[CH:6][C:7]([C:10]([NH:30][C:23]([C:20]3[N:19]=[C:18]([CH3:17])[O:22][N:21]=3)([CH3:29])[CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])=[O:12])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 902033525-Cyclopropyl-4-(2-fluoroethoxy)pyridine-2-carboxylic acidHCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine

Product 1

HCID 902035175-cyclopropyl-4-(2-fluoroethoxy)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-cyclopropyl-4-(2-fluoroethoxy)pyridine-2-carboxylic acid (example 146b) 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 (56 mg, 59%); MS (ESI, m/z): 427.2 (M+H+).

Workup

  1. customisolated (56 mg, 59%)

Sources & evidence

ORD record
ord-a6a7df25585c42cabb7cf2984663f101
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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