2-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)- → (2S,4S)-1-(5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carbonyl)-4-fluoro-pyrrolidine-2-carboxylic acid amide

HRID 624931Notes

Reaction equation

HRID 624931 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.Cl.[F:19][C@@H:20]1[CH2:24][NH:23][C@H:22]([C:25]([NH2:27])=[O:26])[CH2:21]1>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([N:23]3[CH2:24][C@@H:20]([F:19])[CH2:21][C@H:22]3[C:25]([NH2:27])=[O:26])=[O:17])=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 451589172-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)-HCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 90203853(2S,4S)-1-(5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carbonyl)-4-fluoro-pyrrolidine-2-carboxylic acid amide

Procedure

The title compound was synthesized in analogy to Example 47 b, using 5-cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 3 c, 50 mg, 214 μmol) and (2S,4S)-4-fluoro-2-pyrrolidinecarboxamide hydrochloride (1:1) (CAN 426844-23-7; 40 mg, 236 μmol) as starting materials and isolated (68 mg, 91%) as off-white solid; LC-MS (UV peak area, ESI) 100%, 348.1721 [MH+].

Workup

  1. customisolated (68 mg, 91%) as off-white solid

Sources & evidence

ORD record
ord-7d84554f86914816a701a1aa6c7b0853
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

Loading…