Ethyl Acetate → HCID 68520585, compound

HRID 1437422Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]([NH:16][C@H:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH3:18])[C:13]([NH2:26])=[CH:12][CH:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.Cl.[C:28](N)(=N)[CH3:29].C([O-])(O)=O.[Na+].CCOC(C)=O>CCO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]4[N:16]([C@H:17]([C:19]5[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=5)[CH3:18])[C:28]([CH3:29])=[N:26][C:13]4=[CH:12][CH:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of crude (S)—N6-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(4-fluorophenyl)ethyl)pyridine-2,3,6-triamine (Method 9; 0.120 g, 0.34 mmol) and acetamidine hydrochloride (0.052 g, 0.55 mmol) in EtOH (5 ml) was heated at reflux overnight. After cooling to 25° C., saturated NaHCO3 solution (10 ml) and EtOAc (30 ml) were added to the reaction mixture. The organic layer was separated, washed with brine (10 ml), dried over Na2SO4, concentrated, and purified by chromatography (EtOAc:MeOH=100:1) to give the title compound as an off-white solid (0.055 g, 43%). NMR (400 MHz, d6-Acetone) 11.14 (br s, 1H), 8.44 (br s, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.44 (m, 2H), 7.11 (m, 2H), 7.00 (br s, 1H), 6.00 (m, 2H), 2.12 (s, 3H), 2.11 (d, J=7.2 Hz, 3H), 0.89 (m, 2H), 0.65 (m, 2H). MS: Calcd.: 376. Found: [M+H]+ 377.

Workup

temperaturewas heated
temperatureat reflux overnight
customThe organic layer was separated
washwashed with brine (10 ml)
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified by chromatography (EtOAc:MeOH=100:1)

Sources & evidence

ORD record: ord-383df3ff65ad4d43a4355cbe9435bd6f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622482B2

Reaction notes

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