Diisopropylethylamine → (S)-1-[5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carbonyl]-4,4-difluoro-pyrrolidine-2-carboxylic acid amide

HRID 624936

Reaction equation

HRID 624936 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:18]([OH:20])=O)=[N:8][C:9]=2[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:3][CH2:2]1.Cl.[F:22][C:23]1([F:31])[CH2:27][NH:26][C@H:25]([C:28]([NH2:30])=[O:29])[CH2:24]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:18]([N:26]3[CH2:27][C:23]([F:31])([F:22])[CH2:24][C@H:25]3[C:28]([NH2:30])=[O:29])=[O:20])=[N:8][C:9]=2[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 451589094,4-Difluoro-L-prolinamide hydrochlorideHCID 710876985-Cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carboxylic acid

Product 1

HCID 74763820(S)-1-[5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carbonyl]-4,4-difluoro-pyrrolidine-2-carboxylic acid amide

Procedure

In analogy to the procedure described in Example 47 b), 5-cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carboxylic acid (Example 5 g)) was reacted with (S)-4,4-difluoropyrrolidine-2-carboxamide hydrochloride (CAN 426844-51-1) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS (EI): m/e=404.5 [MH+].

Sources & evidence

ORD record
ord-03964169da484a48a1602d95c617e603
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Linked notes

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