3-Amino-3-cyclopropylbutanamide → N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-5-cyclopropyl-4-(1-fluoropropan-2-yloxy)picolinamide

HRID 1480349Notes

Reaction equation

HRID 1480349 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH:14]([CH3:17])[CH2:15][F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[NH2:18][C:19]([CH:25]1[CH2:27][CH2:26]1)([CH3:24])[CH2:20][C:21]([NH2:23])=[O:22]>>[NH2:23][C:21](=[O:22])[CH2:20][C:19]([NH:18][C:10](=[O:12])[C:7]1[CH:6]=[C:5]([O:13][CH:14]([CH3:17])[CH2:15][F:16])[C:4]([CH:1]2[CH2:2][CH2:3]2)=[CH:9][N:8]=1)([CH:25]1[CH2:27][CH2:26]1)[CH3:24]

Participants

3

Reactant 2

HCID 836818103-Amino-3-cyclopropylbutanamideHCID 902040445-Cyclopropyl-4-(1-fluoropropan-2-yloxy)picolinic acid

Product 1

HCID 90204486N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-5-cyclopropyl-4-(1-fluoropropan-2-yloxy)picolinamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-cyclopropyl-4-(1-fluoropropan-2-yloxy)picolinic acid (enantiomer B) (example 289b) and 3-amino-3-cyclopropyl-butanamide (example 270c) as starting materials and isolated (85.4 mg, 80%); MS (ESI, m/z): 364.4 (M+H+).

Workup

  1. customisolated (85.4 mg, 80%)

Sources & evidence

ORD record
ord-33556ff766874bf79c96fb17c25e87d9
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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