Hydrazine hydrate (1:1) → HCID 66990585, compound

HRID 2367213Notes

Reaction equation

HRID 2367213 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1.O.[NH2:26][NH2:27]>CCO>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:27][N:26]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66990645HCID 66990645, compound

Product 1

HCID 66990585HCID 66990585, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-{2-amino-6-[(cyclohexylmethyl)amino]-4-pyrimidinyl}-2-fluorobenzonitrile (300 mg, 0.92 mmol) in EtOH (2 mL) was added hydrazine monohydrate (3.0 mL, 61.2 mmol), and the resulting suspension was stirred at 120° C. for 1 hour under microwave conditions. The clear reaction mixture was concentrated, and the resulting residue was purified by RPHPLC (CH3CN/H2O w/0.1% THF) to afford the title compound (160 mg, 48%) as a light yellow solid. LC-MS (ES) m/z=338 [M+H]+. 1HNMR (400 MHz, DMSO-d6): δ 0.92 (m, 2H), 1.19 (m, 3H), 1.51 (m, 1H), 1.68 (m, 5H), 3.14 (s, 2H), 5.37 (s, 2H), 5.95 (s, 2H), 6.29 (s, 1H), 6.85 (bs, 1H), 7.40 (bs, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.83 (s, 1H), 11.5 (s, 1H).

Workup

  1. concentrationThe clear reaction mixture was concentrated
  2. customthe resulting residue was purified by RPHPLC (CH3CN/H2O w/0.1% THF)

Sources & evidence

ORD record
ord-bcbc11a117774477a7f8f02b15d54d9d
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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