3-(Pyrimidin-2-yl)pyridine-2-carboxylic acid → N-[(1S,2S)-2-{[3-Ethyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

HRID 1750709Notes

Reaction equation

HRID 1750709 reaction equation
[CH2:1]([C:3]1[C:4]([NH:13][C@H:14]2[CH2:18][CH2:17][CH2:16][C@@H:15]2[NH:19][C:20](=[O:33])[C:21]2C=CC=CC=2C2ON=C(C)N=2)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:8]=1)[CH3:2].Cl.C(C1C(N[C@H]2CCC[C@@H]2N)=NC=C(C(F)(F)F)N=1)C.[N:54]1[CH:59]=[CH:58][CH:57]=[N:56][C:55]=1[C:60]1C(C(O)=O)=[N:62][CH:63]=[CH:64][CH:65]=1>>[CH2:1]([C:3]1[C:4]([NH:13][C@H:14]2[CH2:18][CH2:17][CH2:16][C@@H:15]2[NH:19][C:20]([C:21]2[C:60]([C:55]3[N:54]=[CH:59][CH:58]=[CH:57][N:56]=3)=[CH:65][CH:64]=[CH:63][N:62]=2)=[O:33])=[N:5][CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[N:8]=1)[CH3:2]

Participants

4

Reactant 3

HCID 593636623-(Pyrimidin-2-yl)pyridine-2-carboxylic acidHCID 118308090N-[(1S,2S)-2-{[3-Ethyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzamideHCID 118308132(1S,2S)-1-N-[3-Ethyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 118308158N-[(1S,2S)-2-{[3-Ethyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-{[3-ethyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzamide (Example 149) from (1S,2S)-1-N-[3-ethyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 41; 450 mg, 1.64 mmol) and 3-(pyrimidin-2-yl)pyridine-2-carboxylic acid (CAS number 1228431-21-7; 330 mg, 1.64 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d2cff189a8b2475cbeec55617093429d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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