Hydrazine → HCID 58504815, compound

HRID 2367634Notes

Reaction equation

[CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([C:16]2[CH:23]=[C:22]([S:24][CH3:25])[C:19]([C:20]#[N:21])=[C:18](F)[CH:17]=2)[CH:9]=1)[CH3:2].CCN(C(C)C)C(C)C.[NH2:36][NH2:37]>CCO>[CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([C:16]2[CH:17]=[C:18]3[C:19]([C:20]([NH2:21])=[N:36][NH:37]3)=[C:22]([S:24][CH3:25])[CH:23]=2)[CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

In a microwave tube, 4-[6-[(2R)-2-ethyl-1-pyrrolidinyl]-2-(methylamino)-4-pyrimidinyl]-2-fluoro-6-(methylthio)benzonitrile (136 mg, 0.366 mmol), 5 mL of EtOH, Hunig's base (0.064 mL, 0.366 mmol), and hydrazine anhydrous (0.069 mL, 2.197 mmol) were added. The yellow suspension mixture was heated to 100° C. in an oil bath overnight. When the temperature of the reaction reached 100° C., the solid in the mixture was all dissolved. After overnight, there was a white colored solid formed. LCMS showed no more starting material. The reaction was cooled to room temperature, then the white solid was filtered from the yellow solution, washed by CH3CN (2 mL), dried under reduced pressure to afford the title compound (90 mg). LC-MS (ES) m/z=370 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.91 (t, J=7.3 Hz, 3H), 1.36 (m, 1H), 1.80 (m, 2H), 1.93 (m, 3H), 2.59 (s, 3H), 2.83 (d, J=4.6 Hz, 3H), 3.53 (m, 1H), 4.06 (m, 1H), 5.08 (s, 2H), 6.22 (s, 1H), 6.44 (s, 1H), 7.38 (s, 1H), 7.71 (s, 1H), 11.75 (s, 1H).

Workup

customreached 100° C.
customformed
temperatureThe reaction was cooled to room temperature
filtrationthe white solid was filtered from the yellow solution
washwashed by CH3CN (2 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-bb071977a7e1452ca04fa3401174fc6f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

Loading…