Hydrazine hydrate (1:1) → HCID 46216158, compound

HRID 2367268Notes

Reaction equation

HRID 2367268 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]([N:17]([CH3:27])[C@H:18]([CH3:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.O.[NH2:29][NH2:30]>C(O)C>[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]([N:17]([CH3:27])[C@H:18]([CH3:26])[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:30][N:29]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58504394HCID 58504394, compound

Product 1

HCID 46216158HCID 46216158, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 4-(2-amino-6-{methyl[(1R)-1-methyl-2-phenylethyl]amino}-4-pyrimidinyl)-2-fluorobenzonitrile (200 mg, 0.55 mmol) in ethanol (2 mL) was added hydrazine hydrate (2.0 mL, 99%), and the reaction mixture was heated at 120° C. under microwave conditions with stirring for 1 hour. The mixture was cooled to room temperature and concentrated. The resulting residue was washed with Et2O (30 mL) and dried in vacuo to afford the title compound (156 mg) as a yellow solid. LC-MS (ES) m/z=374 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.12 (d, J=6.0 Hz, 3H), 2.77-2.89 (m, 6H), 5.36 (s, 2H), 5.99 (s, 2H), 6.35 (s, 1H), 7.12-7.16 (m, 1H), 7.23-7.27 (m, 4H), 7.49-7.52 (m, 1H), 7.68-7.70 (m, 1H), 7.88 (s, 1H), 11.50 (s, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. washThe resulting residue was washed with Et2O (30 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2fe37e3df21a46f8aef2741a030764b1
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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