Hydrogen Bromide → 5-(1-hydroxycyclobutyl)-N-[1-methyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-methylsulfonyl-ethyl]-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxamide

HRID 1480210Notes

Reaction equation

HRID 1480210 reaction equation
[OH:1][C:2]1([C:6]2[C:7]([O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])=[CH:8][C:9]([C:12]([OH:14])=O)=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:22][C:23]1[O:27][N:26]=[C:25]([C:28]([NH2:35])([CH3:34])[CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])[N:24]=1.Br>>[OH:1][C:2]1([C:6]2[C:7]([O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:18])[F:19])=[CH:8][C:9]([C:12]([NH:35][C:28]([CH3:34])([C:25]3[N:24]=[C:23]([CH3:22])[O:27][N:26]=3)[CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:14])=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineHCID 902040375-(1-hydroxycyclobutyl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid

Product 1

HCID 902034235-(1-hydroxycyclobutyl)-N-[1-methyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-methylsulfonyl-ethyl]-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-(1-hydroxycyclobutyl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid (Example 126c) 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 (13 mg, 40%); MS (ESI, m/z): 507.5 (M+H+).

Workup

  1. customisolated (13 mg, 40%)

Sources & evidence

ORD record
ord-40d0113c6d4b4f92ba7dc2190e322716
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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