3-Amino-3-cyclopropylbutanamide → N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-5-(3-fluorooxetan-3-yl)-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480330Notes

Reaction equation

HRID 1480330 reaction equation
[F: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][O:4][CH2:3]1.[NH2:22][C:23]([CH:29]1[CH2:31][CH2:30]1)([CH3:28])[CH2:24][C:25]([NH2:27])=[O:26]>>[NH2:27][C:25](=[O:26])[CH2:24][C:23]([NH:22][C:12]([C:9]1[CH:8]=[C:7]([O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])[C:6]([C:2]2([F:1])[CH2:3][O:4][CH2:5]2)=[CH:11][N:10]=1)=[O:14])([CH:29]1[CH2:31][CH2:30]1)[CH3:28]

Participants

3

Reactant 2

HCID 836818103-Amino-3-cyclopropylbutanamideHCID 902149505-(3-fluorooxetan-3-yl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid

Product 1

HCID 90204453N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-5-(3-fluorooxetan-3-yl)-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-(3-fluorooxetan-3-yl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid (example 142b) and 3-amino-3-cyclopropyl-butanamide (example 270c) as starting materials and isolated (55 mg, 39%); MS (ESI, m/z): 434.3 (M+H+).

Workup

  1. customisolated (55 mg, 39%)

Sources & evidence

ORD record
ord-a4a0c5e700be4253a0860ac1c4e5e37b
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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