Ethyl Acetate → HCID 11996232, compound

HRID 1092201Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of (S)-N3-(5-cyclopropyl-1H-pyrazol-3-yl)-N1-[1-(4-fluorophenyl)ethyl]benzene-1,3,4-triamine (Method 62; 0.395 g, 1.12 mmol) and formamidine acetate (0.234 g, 2.25 mmol) in EtOH (5 ml) was heated at reflux for 2 hrs. After cooling to 25° C., the reaction mixture was treated with saturated sodium bicarbonate solution (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) to give the title compound as an off-white solid (0.205 g, 50%). NMR (400 MHz) 12.65 (s, 1H), 8.17 (s, 1H), 7.43 (m, 2H), 7.33 (d, J=8.8 Hz, 1H), 7.10 (m, 2H), 6.90 (s, 1H), 6.62 (d, J=8.8 Hz, 1H), 6.25 (d, J=6.4 Hz, 1H), 6.08 (s, 1H), 4.51 (m, 1H), 1.96 (m, 1H), 1.43 (d, J=6.8 Hz, 3H), 1.02 (m, 2H), 0.76 (m, 2H). MS: Calcd.: 361; Found: [M+H]+ 362.

Workup

temperaturewas heated
temperatureat reflux for 2 hrs
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)

Sources & evidence

ORD record: ord-98190e1a4e024a5fa47efe212780f088
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129403B2

Reaction notes

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