(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 66576925, compound

HRID 1409440Notes

Reaction equation

HRID 1409440 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[C:3]1[C:10]1[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=1.[NH2:16][C@@H:17]([CH3:33])[CH2:18][N:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([Cl:32])[CH:25]=2)=[N:20]1>>[Cl:32][C:26]1[CH:25]=[C:24]([C:21]2[CH:22]=[CH:23][N:19]([CH2:18][C@@H:17]([NH:16][C:7]([C:5]3[N:4]=[C:3]([C:10]4[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=4)[N:2]([CH3:1])[CH:6]=3)=[O:9])[CH3:33])[N:20]=2)[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 70981750HCID 70981750, compound

Product 1

HCID 66576925HCID 66576925, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 1-methyl-2-(1-methyl-1H-pyrazol-4-yl)-1H-imidazole-4-carboxylic acid (0.3 g, 1.44 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.377 g, 1.44 mmol). The product was purified by flash chromatography. Yield 200 mg. 1H-NMR (400 MHz; DMSO-d6): δ 1.10 (d, 3H), 3.72 (s, 3H), 3.91 (s, 3H), 4.23-4.45 (m, 3H), 6.95 (d, 1H), 7.63 (d, 1H), 7.83 (t, 2H), 7.99 (d, 1H), 8.03 (d, 1H), 8.07 (s, 1H), 8.17 (s, 1H).

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-365f8d41debe47b0a28aaf99c6d53ff0
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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