3,5-Dimethylphenylboronic acid → N6-(2-{[7-(3,5-Dimethylphenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]amino}ethyl)-3-nitropyridine-2,6-diamine

HRID 2171571Notes

Reaction equation

HRID 2171571 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([NH2:18])[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][CH:13]=2)[N:5]2[N:22]=[CH:23][N:24]=[C:4]2[CH:3]=1.[CH3:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([CH3:32])[CH:31]=1>>[CH3:25][C:26]1[CH:27]=[C:28]([C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]3[N:17]=[C:16]([NH2:18])[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][CH:13]=3)[N:5]3[N:22]=[CH:23][N:24]=[C:4]3[CH:3]=2)[CH:29]=[C:30]([CH3:32])[CH:31]=1

Participants

3

Reactant 2

HCID 27343493,5-Dimethylphenylboronic acidHCID 59312901N6-{2-[(7-Chloro[1,2,4]triazolo[1,5-c]pyrimidin-5-yl)amino]ethyl}-3-nitropyridine-2,6-diamine

Product 1

HCID 59313024N6-(2-{[7-(3,5-Dimethylphenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]amino}ethyl)-3-nitropyridine-2,6-diamine

Procedure

In analogy to the procedure described for Example 94, 39.9 mg (72% of theory) of the product are obtained as a solid starting from 50 mg (0.133 mmol) of N6-{2-[(7-chloro[1,2,4]triazolo-[1,5-c]pyrimidin-5-yl)amino]ethyl}-3-nitropyridine-2,6-diamine (Example 55A) by coupling with 19.9 mg (0.13 mmol) of (3,5-dimethylphenyl)boronic acid and subsequent purification by preparative HPLC.

Workup

  1. customare obtained as a solid

Sources & evidence

ORD record
ord-97f131a1e9214cfe8bb1931567e535b6
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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