2-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine → 5-(1-hydroxycyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

HRID 1480202Notes

Reaction equation

HRID 1480202 reaction equation
[OH:1][C:2]1([C:6]2[C:7]([O:15][CH2:16][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.[CH3:21][S:22]([CH2:25][C:26]([NH2:34])([CH3:33])[C:27]1[N:31]=[C:30]([CH3:32])[O:29][N:28]=1)(=[O:24])=[O:23]>>[OH:1][C:2]1([C:6]2[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:8][C:9]([C:12]([NH:34][C:26]([C:27]3[N:31]=[C:30]([CH3:32])[O:29][N:28]=3)([CH3:33])[CH2:25][S:22]([CH3:21])(=[O:24])=[O:23])=[O:14])=[N:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineHCID 902039115-(1-Hydroxycyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acid

Product 1

HCID 762847525-(1-hydroxycyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-(1-hydroxycyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acid (Example 129b) and 2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (example 109d) as starting materials and isolated (25 mg, 37%); MS (ESI, m/z): 493.3 (M+H+).

Workup

  1. customisolated (25 mg, 37%)

Sources & evidence

ORD record
ord-f35221639d8145a696b6dc70c0e30251
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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