(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 70656120, compound

HRID 872935Notes

Reaction equation

HRID 872935 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:17]=[C:16]([C:18]([OH:20])=O)[NH:15][N:14]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C@@H:22]([CH3:38])[CH2:23][N:24]1[CH:28]=[CH:27][C:26]([C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[C:31]([Cl:37])[CH:30]=2)=[N:25]1>>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:17]=[C:16]([C:18]([NH:21][C@@H:22]([CH3:38])[CH2:23][N:24]3[CH:28]=[CH:27][C:26]([C:29]4[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[C:31]([Cl:37])[CH:30]=4)=[N:25]3)=[O:20])[NH:15][N:14]=2)[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 67172629HCID 67172629, compound

Product 1

HCID 70656120HCID 70656120, compoundYield 44.9%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 3-(1-benzyl-1H-imidazol-4-yl)-1H-pyrazole-5-carboxylic acid (0.268 g, 0.997 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.2 g, 0.767 mmol). The product was purified with flash chromatography. Yield 44.9%. 1H-NMR (400 MHz; CDCl3): δ 1.23 (d, 3H), 4.27 (dd, 1H), 4.41 (dd, 1H), 4.53-4.63 (m, 1H), 5.26 (s, 2H), 6.61 (d, 1H), 6.76 (s, 1H), 7.00-7.05 (m, 2H), 7.28-7.36 (m, 5H), 7.49 (d, 1H), 7.58-7.63 (m, 2H), 7.78 (dd, 1H), 8.03 (s, 1H), 11.75 (bs, 1H).

Workup

  1. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-81773d80233c4829b59c564af8c3e688
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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