Ethyl Acetate → HCID 11560323, compound

HRID 1437423Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH2:27])[C:5]([NH:17][C@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH3:19])=[N:6][C:7]=1[NH:8][C:9]1[CH:13]=[C:12]([CH:14]2[CH2:16][CH2:15]2)[NH:11][N:10]=1.[C:28](O)(=O)C.C(N)=N.C([O-])(O)=O.[Na+].CCOC(C)=O>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[N:27]=[CH:28][N:17]([C@H:18]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[CH3:19])[C:5]2=[N:6][C:7]=1[NH:8][C:9]1[CH:13]=[C:12]([CH:14]2[CH2:16][CH2:15]2)[NH:11][N:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of (S)-5-chloro-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(4-fluorophenyl)ethyl)pyridine-2,3,6-triamine (Method 27; 0.300 g, 0.77 mmol) and formamidine acetate (0.129 g, 1.24 mmol) in EtOH (5 ml) was heated at reflux overnight. After cooling to 25° C., the reaction mixture was treated with saturated NaHCO3 (10 ml) and EtOAc (30 ml). The organic layer was separated, washed with brine (10 ml), and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (EtOAc:MeOH=20:1) to give the title compound as an off-white solid (0.145 g, 47%). NMR (400 MHz) 11.96 (br s, 1H), 8.45 (s, 1H), 8.13 (br s, 1H), 8.12 (s, 1H), 7.36 (m, 2H), 7.16 (m, 1H), 6.18 (s, 1H), 5.87 (br s, 1H), 1.95 (d, J=6.8 Hz, 3H), 1.90 (m, 1H), 0.95 (m, 2H), 0.66 (m, 2H). MS: Calcd.: 396. Found: [M+H]+ 397.

Workup

temperaturewas heated
temperatureat reflux overnight
customThe organic layer was separated
washwashed with brine (10 ml)
dry with materialdried over Na2SO4
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (EtOAc:MeOH=20:1)

Sources & evidence

ORD record: ord-8ae13c8f5c004f878be5286e0cd5fb48
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622482B2

Reaction notes

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