3-(Pyrrolidino)phenylboronic acid → 3-Nitro-N6-(2-{[7-(3-pyrrolidin-1-ylphenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]amino}-ethyl)pyridine-2,6-diamine

HRID 2171573Notes

Reaction equation

HRID 2171573 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.[N:25]1([C:30]2[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1>>[N+:19]([C:15]1[C:16]([NH2:18])=[N:17][C:12]([NH:11][CH2:10][CH2:9][NH:8][C:6]2[N:5]3[N:22]=[CH:23][N:24]=[C:4]3[CH:3]=[C:2]([C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([N:25]4[CH2:26][CH2:27][CH2:28][CH2:29]4)[CH:31]=3)[N:7]=2)=[CH:13][CH:14]=1)([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 41926693-(Pyrrolidino)phenylboronic 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 593130953-Nitro-N6-(2-{[7-(3-pyrrolidin-1-ylphenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]amino}-ethyl)pyridine-2,6-diamine

Procedure

In analogy to the procedure described for Example 94, 17.5 mg (28% 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 25.3 mg (0.13 mmol) of (3-pyrrolidin-1-ylphenyl)boronic acid and subsequent purification by preparative HPLC.

Workup

  1. customare obtained as a solid

Sources & evidence

ORD record
ord-b7712140aa034b2cb30fada011f9fdb4
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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