(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 86714675, compound

HRID 1409467Notes

Reaction equation

HRID 1409467 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=1)=[O:5])[CH3:2].[NH2:22][C@@H:23]([CH3:40])[CH2:24][N:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:37]=[C:36]([F:38])[C:33]([C:34]#[N:35])=[C:32]([Cl:39])[CH:31]=2)=[N:26]1>>[Cl:39][C:32]1[CH:31]=[C:30]([C:27]2[CH:28]=[CH:29][N:25]([CH2:24][C@@H:23]([NH:22][C:11]([C:9]3[N:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=3)=[O:13])[CH3:40])[N:26]=2)[CH:37]=[C:36]([F:38])[C:33]=1[C:34]#[N:35]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70981146HCID 70981146, compound

Product 1

HCID 86714675HCID 86714675, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 2-(ethoxycarbonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (3.18 mmol, 1 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (3.18 mmol, 890 mg). The product was purified by flash-chromatography. Yield 1.6 g. 1H-NMR (400 MHz; DMSO-d6): δ −0.01 (s, 9H), 0.80 (t, 2H), 1.15 (d, 3H), 1.30 (t, 3H), 3.48 (t, 2H), 4.34-4.49 (m, 5H), 5.69 (s, 2H), 6.98 (d, 1H), 7.78-7.82 (m, 2H), 7.87 (s, 1H), 8.03 (s, 1H), 8.21 (d, 1H). LC-MS: [M+1]=575.11.

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-40f1031f3f2a4de49ff3c2c6cba18ad7
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…