Hydrazine hydrate (1:1) → HCID 58504480, compound

HRID 2367517Notes

Reaction equation

HRID 2367517 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([N:16]3[C@H:21]([CH3:22])[CH2:20][O:19][C@H:18]([CH2:23][OH:24])[CH2:17]3)[N:13]=[C:12]([NH:25][CH3:26])[N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O.[NH2:28][NH2:29]>CCO>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][C:8]([C:10]3[N:11]=[C:12]([NH:25][CH3:26])[N:13]=[C:14]([N:16]4[C@H:21]([CH3:22])[CH2:20][O:19][C@H:18]([CH2:23][OH:24])[CH2:17]4)[CH:15]=3)=[CH:7][CH:6]=2)[NH:29][N:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58504779HCID 58504779, compound

Product 1

HCID 58504480HCID 58504480, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoro-4-[6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-2-(methylamino)-4-pyrimidinyl]benzonitrile (151 mg, 0.42 mmol) and hydrazine monohydrate (0.41 mL, 8.44 mmol) in EtOH (4 mL) was stirred at 100° C. in a sealed tube for 42 hours. It was then cooled, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (24 g SiO2, CH2Cl2 to 90/10/1 CH2Cl2/CH3OH/NH4OH gradient) to give the title compound (113 mg) as a white solid. LC-MS (ES) m/z=370 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.17 (d, J=6.6 Hz, 3H), 2.72-2.93 (m, 4H), 3.37-3.59 (m, 3H), 3.66 (d, J=11.2 Hz, 1H), 3.77 (d, J=11.1 Hz, 1H), 3.94-4.74 (bs, 2H), 4.38 (t, J=5.7 Hz, 1H), 5.38 (s, 2H), 6.54 (m, 2H), 7.59 (d, J=8.3 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.98 (s, 1H), 11.50 (s, 1H).

Workup

  1. temperatureIt was then cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (24 g SiO2, CH2Cl2 to 90/10/1 CH2Cl2/CH3OH/NH4OH gradient)

Sources & evidence

ORD record
ord-ed91e1bf15a74de7a3295a3dea4814e3
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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