Potassium cyclopropyltrifluoroborate → N-((S)-1-amino-4-methyl-1-oxopentan-2-yl)-5-cyclopropyl-6-((tetrahydrofuran-2-yl)methoxy)picolinamide

HRID 632248

Reaction equation

[C:1]([C@@H:4]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15](Br)=[C:14]([O:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)[N:13]=1)=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:3])[NH2:2].[CH:26]1([B-](F)(F)F)[CH2:28][CH2:27]1.[K+]>>[NH2:2][C:1](=[O:3])[C@@H:4]([NH:9][C:10](=[O:11])[C:12]1[CH:17]=[CH:16][C:15]([CH:26]2[CH2:28][CH2:27]2)=[C:14]([O:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)[N:13]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

Reactant 2

HCID 23697338Potassium cyclopropyltrifluoroborate

HCID 711056435-Bromo-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid ((S)-1-carbamoyl-3-methyl-butyl)-amide

Product 1

HCID 71087442N-((S)-1-amino-4-methyl-1-oxopentan-2-yl)-5-cyclopropyl-6-((tetrahydrofuran-2-yl)methoxy)picolinamide

Procedure

The title compound was synthesized in analogy to Example 166 b, using 5-bromo-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid ((S)-1-carbamoyl-3-methyl-butyl)-amide (Example 186 a) and potassium cyclopropyltrifluoroborate as starting materials, MS (EI): m/e=376.2 [M+H]+.

Sources & evidence

ORD record: ord-59c5b9a56c814ad99fe410e364a28697
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321727B2

Linked notes

Loading…