Hydrazine hydrate (1:1) → (R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-(trifluoromethyl)benzonitrile

HRID 872555Notes

Reaction equation

HRID 872555 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@H:12]([CH3:31])[CH2:13][N:14]1[CH:18]=[CH:17][C:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=2)=[N:15]1.O.NN>C(O)C>[NH2:3][C@H:12]([CH3:31])[CH2:13][N:14]1[CH:18]=[CH:17][C:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=2)=[N:15]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70657475(R)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-(trifluoromethyl)benzonitrile

Product 1

HCID 67180702(R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-(trifluoromethyl)benzonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-(trifluoromethyl)benzonitrile (0.199 g, 0.469 mmol) was mixed with ethanol (15 ml). Hydrazine hydrate (0.227 ml, 4.69 mmol) was added and the mixture was refluxed for 3 h. After cooling to RT the precipitate was filtered and washed with ethanol. The filtrate was purified with CombiFlash using DCM and methanol as eluents. Drying in the vacuum afforded 0.080 g of the title product. 1H-NMR (400 MHz; d6-DMSO): δ 0.96 (d, 3H), 3.21-3.29 (m, 2H), 4.01-4.03 (m, 2H), 7.05 (d, 1H), 7.88 (d, 2H), 8.18 (d, 1H), 8.26-8.28 (m, 1H), 8.31 (s, 1H).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationwas filtered
  3. washwashed with ethanol
  4. customThe filtrate was purified with CombiFlash
  5. customDrying in the vacuum

Sources & evidence

ORD record
ord-2678c411b17e4afda12cc481996492a9
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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