HCID 66785913, compound → HCID 71735754, compound

HRID 1615923Notes

Reaction equation

HRID 1615923 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:9]([CH2:12][CH:13]3[CH2:15][CH2:14]3)=[N:10][N:11]=2)[CH:5]=[CH:6][C:7]=1I.[NH2:16][CH2:17][CH:18]1[CH2:20][CH:19]1[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>>[Cl:1][C:2]1[C:3]2[N:4]([C:9]([CH2:12][CH:13]3[CH2:15][CH2:14]3)=[N:10][N:11]=2)[CH:5]=[CH:6][C:7]=1[NH:16][CH2:17][CH:18]1[CH2:20][CH:19]1[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

Participants

3

Reactant 2

HCID 66785913HCID 66785913, compoundHCID 86696517HCID 86696517, compound

Product 1

HCID 71735754HCID 71735754, compoundYield 35.3%

Procedure

A mixture of 8-chloro-3-(cyclopropyl methyl)-7-iodo-[1,2,4]triazolo[4,3-a]pyridine (60 mg, 0.180 mmol), 2-(2-(aminomethyl)cyclopropyl)benzonitrile (31.0 mg, 0.180 mmol) was reacted in a manner similar to Example 1 to give 2-(2-(((8-chloro-3-(cyclopropylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)amino)methyl)cyclopropyl)benzonitrile (24 mg, 32.5%) as a film. 1H NMR (400 MHz, METHANOL-d4) δ 8.15 (d, J=7.5 Hz, 1H), 7.62 (dd, J=7.8, 1.0 Hz, 1H), 7.53 (td, J=7.8, 1.3 Hz, 1H), 7.29 (td, J=7.7, 1.0 Hz, 1H), 7.11 (d, J=8.0 Hz, 1H), 6.97 (d, J=7.8 Hz, 1H), 3.65 (dd, J=14.6, 6.0 Hz, 1H), 3.51 (dd, J=14.6, 6.5 Hz, 1H), 2.98 (d, J=6.8 Hz, 2H), 2.28-2.20 (m, 1H), 1.55 (ddd, J=8.7, 6.1, 4.8 Hz, 1H), 1.26-1.08 (m, 3H), 0.65-0.54 (m, 2H), 0.36-0.25 (m, 2H). LCMS: M+1=378.0.

Workup

  1. customwas reacted in a manner similar to Example 1

Sources & evidence

ORD record
ord-33597314fe454d1c9376a8f1d8f6a6fe
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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