4,4-Difluoro-L-prolinamide hydrochloride → (2S)-1-[6-(Cyclopropylmethoxy)-5-(1-fluorocyclobutyl)pyridine-2-carbonyl]-4,4-difluoropyrrolidine-2-carboxamide

HRID 624997Notes

Reaction equation

HRID 624997 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[C:15]2([F:19])[CH2:18][CH2:17][CH2:16]2)[CH2:3][CH2:2]1.Cl.[F:21][C:22]1([F:30])[CH2:26][NH:25][C@H:24]([C:27]([NH2:29])=[O:28])[CH2:23]1>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:25]3[CH2:26][C:22]([F:30])([F:21])[CH2:23][C@H:24]3[C:27]([NH2:29])=[O:28])=[O:14])[CH:9]=[CH:8][C:7]=2[C:15]2([F:19])[CH2:18][CH2:17][CH2:16]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 451589094,4-Difluoro-L-prolinamide hydrochlorideHCID 902026076-(Cyclopropylmethoxy)-5-(1-fluorocyclobutyl)pyridine-2-carboxylic acid

Product 1

HCID 90203864(2S)-1-[6-(Cyclopropylmethoxy)-5-(1-fluorocyclobutyl)pyridine-2-carbonyl]-4,4-difluoropyrrolidine-2-carboxamideYield 91%

Procedure

In analogy to the procedure described in Example 127 e), 6-(cyclopropylmethoxy)-5-(1-fluorocyclobutyl)pyridine-2-carboxylic acid (Example 130 f, 20 mg, 49.8 μmol) was reacted with (S)-4,4-difluoropyrrolidine-2-carboxamide hydrochloride (CAN 426844-51-1, 11.1 mg, 59.7 μmol) to give the title compound (18 mg, 91%) as off-white solid, MS (EI): m/e=398.4 [MH+].

Sources & evidence

ORD record
ord-8d7db6ea59e54dee96804538cdfcfceb
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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