Aminopyrazine → (S)-N2-[1-(4-fluorophenyl)ethyl]-N2-methyl-4-(1-methyl-1H-pyrazol-4-yl)-N6-(pyrazin-2-yl)pyridine-2,6-diamine

HRID 1187735Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]([C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[CH3:9])[CH:5]=[C:4]([C:19]2[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=2)[CH:3]=1.[NH2:25][C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C@@H:10]([N:8]([CH3:9])[C:6]2[CH:5]=[C:4]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[CH:3]=[C:2]([NH:25][C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)[N:7]=2)[CH3:11])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

60 mg of (S)-6-chloro-N-[1-(4-fluorophenyl)ethyl]-N-methyl-4-(1-methyl-1H-pyrazol-4-yl)pyridine-2-amine, 18 mg of 2-aminopyrazine, 16 mg of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 24 mg of sodium t-butoxide and 9 mg of tris(dibenzylideneacetone)(chloroform)dipalladium were added in turn to 2 ml of degassed toluene, and the mixture was stirred at 100° C. for 1 hour under argon atmosphere. The reaction solution was purified by silica gel column chromatography to obtain 60 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-N2-methyl-4-(1-methyl-1H-pyrazol-4-yl)-N6-(pyrazin-2-yl)pyridine-2,6-diamine as pale yellow oil. Furthermore, the obtained compound was subjected to hydrochlorination using a conventional method to obtain 29 mg of the objective compound as pale yellow powder.

Workup

customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-33a651e7328d4b17bf351b17e3e3681e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673891B2

Reaction notes

Loading…