HCID 12088083, compound → HCID 71735755, compound

HRID 1615924Notes

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.[N:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:24][CH:23]2[CH2:25][NH2:26])=[CH:18][CH:17]=1>>[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:26][CH2:25][CH:23]1[CH2:24][CH:22]1[C:19]1[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=1

Participants

Reactant 2

HCID 12088083HCID 12088083, compound

HCID 66785913HCID 66785913, compound

Product 1

HCID 71735755HCID 71735755, compoundYield 48.4%

Procedure

A mixture of 8-chloro-3-(cyclopropylmethyl)-7-iodo-[1,2,4]triazolo[4,3-a]pyridine (50 mg, 0.150 mmol) and (2-(pyridin-4-yl)cyclopropyl)methanamine (26.7 mg, 0.180 mmol) was reacted in a manner similar to Example 1 to give 8-chloro-3-(cyclopropylmethyl)-N-((2-(pyridin-4-yl)cyclopropyl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-7-amine (25.7 mg, 47.5%). 1H NMR (500 MHz, DMSO-d6) δ 8.35 (d, J=6.1 Hz, 2H), 8.23 (d, J=7.6 Hz, 1H), 7.06 (d, J=6.1 Hz, 2H), 6.90 (d, J=7.6 Hz, 1H), 6.42 (t, J=6.1 Hz, 1H), 2.95 (d, J=6.7 Hz, 2H), 1.95 (dd, J=8.7, 4.4 Hz, 1H), 1.48 (br. s., 1H), 1.19-1.09 (m, 2H), 1.09-1.00 (m, 1H), 0.50 (d, J=6.4 Hz, 2H), 0.25 (d, J=4.6 Hz, 2H). LCMS: M+1=354.2.

Workup

customwas reacted in a manner similar to Example 1

Sources & evidence

ORD record: ord-43699ee595044478946c32806422f79d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765767B2

Reaction notes

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