Hydrazine hydrate (1:1) → (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile

HRID 872463Notes

Reaction equation

HRID 872463 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@@H:12]([CH3:28])[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]([CH3:27])[CH:20]=2)=[N:15]1.O.NN>>[NH2:3][C@@H:12]([CH3:28])[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]([CH3:27])[CH:20]=2)=[N:15]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70657327(S)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile

Product 1

HCID 67172666(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-methylbenzonitrileYield 19%

Procedure

(S)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile (481 mg, 1.3 mmol) was treated with hydrazine hydrate using the method of Example 27(b). Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-20% MeOH/DCM) to obtain 59 mg (19%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 0.96 (d, 3H), 2.52 (s, 3H), 3.23 (m, 1H), 4.00 (m, 2H), 6.85 (d, 1H), 7.77 (m, 2H), 7.81 (d, 1H), 7.89 (m, 1H).

Workup

  1. customCrude product was purified by chromatography (CombiFlash, silica column, eluent: 0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-5e5466b6389b4bee98ac1de03d3752c5
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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