3-Cyclopropylpicolinic acid → 3-Cyclopropyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

HRID 1750630Notes

Reaction equation

HRID 1750630 reaction equation
FC(F)(F)C1C=CC=CC=1[C:5]([NH:7][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:13][C:14]1[CH:19]=[N:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1)=[O:6].Cl.FC(F)(F)C1N=CC(N[C@H]2CCC[C@@H]2N)=NC=1.[CH:48]1([C:51]2[C:52](C(O)=O)=[N:53][CH:54]=[CH:55][CH:56]=2)[CH2:50][CH2:49]1>>[CH:48]1([C:51]2[C:52]([C:5]([NH:7][C@H:8]3[CH2:12][CH2:11][CH2:10][C@@H:9]3[NH:13][C:14]3[CH:19]=[N:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=3)=[O:6])=[N:53][CH:54]=[CH:55][CH:56]=2)[CH2:50][CH2:49]1

Participants

4

Reactant 3

HCID 686851453-Cyclopropylpicolinic acid2×HCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 118308264HCID 118308264, compound

Product 1

HCID 1183081933-Cyclopropyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

Procedure

Prepared according to the procedure for 2-(trifluoromethyl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 62) from (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14; 75 mg, 0.30 mmol) and 3-cyclopropylpyridine-2-carboxylic acid (Intermediate 16; 50 mg, 0.31 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-92a56e600928416795142564961f063d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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