(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 86714661, compound

HRID 1409433Notes

Reaction equation

HRID 1409433 reaction equation
[CH:1]([C:4]1[N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=1)([CH3:3])[CH3:2].[NH2:20][C@@H:21]([CH3:37])[CH2:22][N:23]1[CH:27]=[CH:26][C:25]([C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([Cl:36])[CH:29]=2)=[N:24]1>>[Cl:36][C:30]1[CH:29]=[C:28]([C:25]2[CH:26]=[CH:27][N:23]([CH2:22][C@@H:21]([NH:20][C:9]([C:7]3[N:8]=[C:4]([CH:1]([CH3:2])[CH3:3])[N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=3)=[O:11])[CH3:37])[N:24]=2)[CH:35]=[CH:34][C:31]=1[C:32]#[N:33]

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 86714660HCID 86714660, compound

Product 1

HCID 86714661HCID 86714661, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 2-isopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (0.430 g, 1.5 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.395 g, 1.5 mmol). Yield 360 mg. 1H-NMR (400 MHz; DMSO-d6): δ 0.06 (s, 9H), 0.80-0.85 (m, 2H), 1.10 (d, 3H), 1.21-1.24 (m, 6H), 3.08-3.15 (m, 1H), 3.43-3.47 (m, 2H), 4.30-4.44 (m, 3H), 5.32 (s, 2H), 6.96 (d, 1H), 7.63 (s, 1H), 7.85-7.87 (m, 2H), 7.93-7.95 (m, 2H), 8.09 (s, 1H).

Sources & evidence

ORD record
ord-a8f33c82b3614f538ae66b47c145ee46
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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