2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine → 5-cyclopropyl-N-[1-cyclopropyl-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-yl]-4-(2,2-difluoroethoxy)pyridine-2-carboxamide

HRID 1480218Notes

Reaction equation

HRID 1480218 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.[CH:18]1([CH2:21][C:22]([NH2:30])([CH3:29])[C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH2:20][CH2:19]1>>[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:30][C:22]([C:23]3[N:27]=[C:26]([CH3:28])[O:25][N:24]=3)([CH3:29])[CH2:21][CH:18]3[CH2:19][CH2:20]3)=[O:12])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 710877912-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamineHCID 902035305-Cyclopropyl-4-(2,2-difluoroethoxy)pyridine-2-carboxylic acid

Product 1

HCID 902040665-cyclopropyl-N-[1-cyclopropyl-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-yl]-4-(2,2-difluoroethoxy)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-cyclopropyl-4-(2,2-difluoroethoxy)pyridine-2-carboxylic acid (Example 145d) and 2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (example 66e) as starting materials and isolated (66 mg, 72%); MS (ESI, m/z): 407.6 (M+H+).

Workup

  1. customisolated (66 mg, 72%)

Sources & evidence

ORD record
ord-6b603f3d53794ceb8ec3e80e3a30a67f
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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