3,3-Difluoropyrrolidine → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid [4-(3,3-difluoro-pyrrolidine-1-carbonyl)-pyridin-3-yl]-amide

HRID 467682Notes

Reaction equation

HRID 467682 reaction equation
[F:1][C:2]1([F:7])[CH2:6][CH2:5][NH:4][CH2:3]1.[CH:8]1([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[CH:28]=[N:27][CH:26]=[CH:25][C:21]=3[C:22](O)=[O:23])=[O:18])[C:14]([NH:29][C:30]3[CH:31]=[N:32][CH:33]=[N:34][CH:35]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1>>[F:1][C:2]1([F:7])[CH2:6][CH2:5][N:4]([C:22]([C:21]2[CH:25]=[CH:26][N:27]=[CH:28][C:20]=2[NH:19][C:17]([C:15]2[C:14]([NH:29][C:30]3[CH:31]=[N:32][CH:33]=[N:34][CH:35]=3)=[CH:13][CH:12]=[C:11]([CH:8]3[CH2:10][CH2:9]3)[N:16]=2)=[O:18])=[O:23])[CH2:3]1

Participants

3

Reactant 2

HCID 27828273,3-DifluoropyrrolidineHCID 700980543-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-isonicotinic acid

Product 1

HCID 547605676-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid [4-(3,3-difluoro-pyrrolidine-1-carbonyl)-pyridin-3-yl]-amideYield 27%

Procedure

According to the general method described in step 3 of example 53, reaction of 3,3-difluoro-pyrrolidine with 3-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-isonicotinic acid provided the title compound (27%) as amourphous light yellow solid.

Sources & evidence

ORD record
ord-16acc821bba145a6ae3ffc6500471682
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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