N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethyl)pyrimidine-2,4-diamine → N2-(1-(3H-imidazo[4,5-c]pyridin-6-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 2409080Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]([C:19]4[N:24]=[CH:23][C:22]5[N:25](CC6C=CC(OC)=CC=6)[CH:26]=[N:27][C:21]=5[CH:20]=4)[CH3:18])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[N:27]1[C:21]2[CH:20]=[C:19]([CH:17]([NH:16][C:12]3[N:11]=[C:10]([NH:9][C:6]4[CH:5]=[C:4]([CH:1]5[CH2:3][CH2:2]5)[NH:8][N:7]=4)[CH:15]=[CH:14][N:13]=3)[CH3:18])[N:24]=[CH:23][C:22]=2[NH:25][CH:26]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethyl)pyrimidine-2,4-diamine (130 mg, 0.27 mmol) in TFA (3 mL) was heated at 70° C. for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to afford 45 mg (46%) of N2-(1-(3H-imidazo[4,5-c]pyridin-6-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-d6ad5b0c811545d2ae897f51ae7018f0
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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