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

HRID 2171572Notes

Reaction equation

HRID 2171572 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.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=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:30]3[CH:31]=[CH:32][C:27]([C:26]([F:37])([F:36])[F:25])=[CH:28][CH:29]=3)[N:7]=2)=[CH:13][CH:14]=1)([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)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 593129573-Nitro-N6-[2-({7-[4-(trifluoromethyl)phenyl][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, 2.3 mg (4% of theory) of the product are obtained as 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 25.2 mg (0.13 mmol) of [4-(trifluoromethyl)phenyl]boronic acid and subsequent purification by preparative HPLC.

Workup

  1. customare obtained as solid

Sources & evidence

ORD record
ord-bcae831ce8174bf0b05ac0518bca750b
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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