HCID 67168497, compound → HCID 70656573, compound

HRID 872675Notes

Reaction equation

HRID 872675 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[O:12][CH:13]=[C:14]([C:16]([OH:18])=O)[N:15]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[NH2:19][C@@H:20]([CH3:36])[CH2:21][N:22]1[CH:26]=[CH:25][C:24]([C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([Cl:35])[CH:28]=2)=[N:23]1>>[Cl:35][C:29]1[CH:28]=[C:27]([C:24]2[CH:25]=[CH:26][N:22]([CH2:21][C@@H:20]([NH:19][C:16]([C:14]3[N:15]=[C:11]([CH:8]4[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:10][CH2:9]4)[O:12][CH:13]=3)=[O:18])[CH3:36])[N:23]=2)[CH:34]=[CH:33][C:30]=1[C:31]#[N:32]

Participants

3

Reactant 2

HCID 67168497HCID 67168497, compoundHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656573HCID 70656573, compoundYield 87%

Procedure

(S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(1-(methylsulfonyl)piperidin-4-yl)oxazole-4-carboxamide was prepared using the method of Example 34(d) starting from 2-(1-(methylsulfonyl)piperidin-4-yl)oxazole-4-carboxylic acid (0.4 g, 01.458 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.317 g, 01.215 mmol). The product was purified by extracting it from DCM with 0.1 M HCl, 1 M Na2CO3, water and brine. Yield 87%. 1H-NMR (400 MHz; CDCl3): δ 1.25 (d, 3H), 1.97 (m, 2H), 2.15 (m, 2H), 2.83 (s, 3H), 2.89 (m, 3H), 3.81 (m, 2H), 4.30 (dd, 1H), 4.41 (dd, 1H), 4.57 (m, 1H), 6.63 (d, 1H), 7.46 (d, 1H), 7.49 (d, 1H), 7.68 (dd, 1H), 7.79 (dd, 1H), 8.01 (dd, 1H), 8.11 (s, 1H).

Workup

  1. customThe product was purified
  2. extractionby extracting it from DCM with 0.1 M HCl, 1 M Na2CO3, water and brine

Sources & evidence

ORD record
ord-887edcdb22d24f71bb85101354eebd42
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…