Methylhydrazine → HCID 71093641, compound

HRID 72701Notes

Reaction equation

[N:1]1([C:5]2[C:10]([C:11]([C:13]3[CH:14]=[N:15][N:16]([CH3:25])[C:17]=3[C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=O)=[C:9](Cl)[N:8]=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:27][NH:28][NH2:29]>N1C=CC=CC=1>[N:1]1([C:5]2[N:6]=[CH:7][N:8]=[C:9]3[N:28]([CH3:27])[N:29]=[C:11]([C:13]4[CH:14]=[N:15][N:16]([CH3:25])[C:17]=4[C:18]4[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=4)[C:10]=23)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl][1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone (C6) (from Step 6, ≦0.576 mmol) in pyridine (5.0 mL) was added methylhydrazine (0.302 mL, 5.74 mmol), and the reaction was stirred at 85° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified via silica gel chromatography (Gradient: 0 to 30% methanol in dichloromethane) to provide the title product as a colorless oil. Yield: 200 mg, 0.556 mmol, 97% over two steps. LCMS m/z 360.5 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.21-2.30 (m, 2H), 2.34 (br s, 3H), 3.75-4.04 (br m, 4H), 3.91 (s, 3H), 3.99 (s, 3H), 7.20 (br AB quartet, JAB=8.1 Hz, ΔνAB=33 Hz, 4H), 7.67 (s, 1H), 8.32 (s, 1H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified via silica gel chromatography (Gradient: 0 to 30% methanol in dichloromethane)

Sources & evidence

ORD record: ord-be494788cf1346dab79e02c23f41d422
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829010B2

Reaction notes

Loading…