Hydrazine hydrate (1:1) → HCID 66991409, compound

HRID 2367201Notes

Reaction equation

HRID 2367201 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[C:14](F)[C:11]([C:12]#[N:13])=[C:10]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[C:22]([CH3:27])=[N:23][NH:24][C:25]=3[CH3:26])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.O.[NH2:29][NH2:30]>CCO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[C:25]([CH3:26])=[N:24][NH:23][C:22]=3[CH3:27])[C:11]3[C:12]([NH2:13])=[N:29][NH:30][C:14]=3[CH:15]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66990954HCID 66990954, compound

Product 1

HCID 66991409HCID 66991409, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(2-amino-4-pyrimidinyl)-2-{[3-(3,5-dimethyl-1H-pyrazol-4-yl)propyl]amino}-6-fluorobenzonitrile (22 mg, 0.037 mmol) in EtOH (2 mL) was added hydrazine monohydrate (1 mL). The resulting solution was stirred at 90° C. until the starting material was consumed as judged by LCMS (˜12 hours). The reaction mixture was concentrated, and the resulting yellow solid was dissolved in EtOH and precipitated with hexanes. The filtrate was decanted to afford the title compound (5 mg, 32%) as a light yellow solid. LC-MS (ES) m/z=378 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 1.91-1.98 (m, 2H), 2.16-2.23 (s, 6H), 2.59 (t, J=7.2 Hz, 2H), 3.24-3.31 (m, 2H), 6.60 (s, 1H), 7.04 (d, J=5.3 Hz, 1H), 7.23 (s, 1H), 8.27 (d, J=5.30 Hz, 1H).

Workup

  1. customwas consumed
  2. customas judged by LCMS (˜12 hours)
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe resulting yellow solid was dissolved in EtOH
  5. customprecipitated with hexanes
  6. customThe filtrate was decanted

Sources & evidence

ORD record
ord-85e5d148db7541df9a531793cf847fc6
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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