(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 67171876, compound

HRID 872892Notes

Reaction equation

HRID 872892 reaction equation
[C:1]([C:4]1[C:8]([Cl:9])=[C:7]([C:10]([OH:12])=O)[NH:6][N:5]=1)(=[O:3])[CH3:2].[NH2:13][C@@H:14]([CH3:30])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[CH:22]=2)=[N:17]1>>[C:1]([C:4]1[C:8]([Cl:9])=[C:7]([C:10]([NH:13][C@@H:14]([CH3:30])[CH2:15][N:16]2[CH:20]=[CH:19][C:18]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[CH:22]=3)=[N:17]2)=[O:12])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 67172375HCID 67172375, compound

Product 1

HCID 67171876HCID 67171876, compoundYield 30.8%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 3-acetyl-4-chloro-1H-pyrazole-5-carboxylic acid (0.527 g, 2.79 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.56 g, 2.148 mmol). The product was purified by reverse phase flash chromatography. Yield 30.8%. 1H-NMR (400 MHz; DMSO-d6): δ 1.16 (d, 3H), 2.54 (s, 3H), 4.31 (dd, 1H), 4.37 (dd, 1H), 4.42-4.51 (m, 1H), 6.95 (d, 1H), 7.84 (d, 1H), 7.94 (dd, 1H), 7.98 (d, 1H), 8.06 (d, 1H), 8.27 (bs, 1H), 14.45 (s, 1H).

Workup

  1. customThe product was purified by reverse phase flash chromatography

Sources & evidence

ORD record
ord-74a325f29a6a42be96bc1b1b3f493bb5
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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