(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 86714678, compound

HRID 1409471Notes

Reaction equation

HRID 1409471 reaction equation
[CH2:1]([O:3][C:4]([C:7]1[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=1)([CH3:6])[CH3:5])[CH3:2].[NH2:23][C@@H:24]([CH3:41])[CH2:25][N:26]1[CH:30]=[CH:29][C:28]([C:31]2[CH:38]=[C:37]([F:39])[C:34]([C:35]#[N:36])=[C:33]([Cl:40])[CH:32]=2)=[N:27]1>>[Cl:40][C:33]1[CH:32]=[C:31]([C:28]2[CH:29]=[CH:30][N:26]([CH2:25][C@@H:24]([NH:23][C:12]([C:10]3[N:11]=[C:7]([C:4]([O:3][CH2:1][CH3:2])([CH3:5])[CH3:6])[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=3)=[O:14])[CH3:41])[N:27]=2)[CH:38]=[C:37]([F:39])[C:34]=1[C:35]#[N:36]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70980874HCID 70980874, compound

Product 1

HCID 86714678HCID 86714678, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 2-(2-ethoxypropan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (1.15 mmol, 380 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (1.15 mmol, 320 mg). The product was purified by flash-chromatography. Yield 260 mg. 1H-NMR (400 MHz; DMSO-d6): δ −0.01 (s, 9H), 0.80-0.91 (m, 5H), 0.94 (t, 3H), 1.23 (s, 6H), 3.21 (q, 2H), 3.58 (t, 2H), 4.33-4.42 (m, 2H), 4.53-4.59 (m, 1H), 5.53 (s, 2H), 6.61 (d, 1H), 7.41 (d, 1H), 7.52 (d, 1H), 7.59 (d, 1H), 7.64 (s, 1H), 7.74 (s, 1H). LC-MS: [M+1]=589.23.

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-affb80ccac8148718e581ed45f6713c2
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…