2-Bromo-4-(trifluoromethyl)pyridine → 2-(2H-1,2,3-Triazol-2-yl)-N-[(1S,2S)-2-{[4-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

HRID 1750684Notes

Reaction equation

HRID 1750684 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:14][C:15](=[O:27])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:22]2[N:26]=[CH:25][CH:24]=[N:23]2)=[N:6][CH:7]=1.Cl.N[C@H]1CCC[C@@H]1NC(=O)C1C=CC=CC=1N1N=CC=N1.BrC1C=C([C:56]([F:59])([F:58])[F:57])C=CN=1>>[N:23]1[N:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([NH:14][C@H:10]2[CH2:11][CH2:12][CH2:13][C@@H:9]2[NH:8][C:5]2[CH:4]=[C:3]([C:56]([F:59])([F:58])[F:57])[CH:2]=[CH:7][N:6]=2)=[O:27])[N:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 27815432-Bromo-4-(trifluoromethyl)pyridineHCID 118025476N-[(1S,2S)-2-Aminocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride2×HCID 118308185N-[(1S,2S)-2-[(5-Bromopyridin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

Product 1

HCID 1183081292-(2H-1,2,3-Triazol-2-yl)-N-[(1S,2S)-2-{[4-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

Conditions

Temperature
140 °C

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-[(5-bromopyridin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Example 118) from N-[(1S,2S)-2-aminocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 4; 200 mg, 0.65 mmol) and 2-bromo-4-(trifluoromethyl)pyridine (CAS number 175205-81-9; 147 mg, 0.650 mmol) except this was heated to 140° C. for 17 hours to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a7991aac84be4bd7a93ef7f9b77d3596
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…