Morpholine → HCID 59631827, compound

HRID 2369055Notes

Reaction equation

HRID 2369055 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)=[CH:11][CH:12]=2)[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[N:4]=1.C([O-])([O-])=O.[K+].[K+].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CC#N>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:5]1[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:14]=3)=[CH:11][CH:12]=2)=[CH:7][C:3]([CH2:2][N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[N:4]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 59632228HCID 59632228, compound

Product 1

HCID 59631827HCID 59631827, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromomethyl-1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-thiophen-2-yl]-1H-pyrazole (51 mg, 0.1 mmol), K2CO3 (42 mg, 0.3 mmol), KI (10 mg), and morpholine (0.3 mmol) in anhydrous MeCN (5 mL) was stirred at 90° C. for 6 h under N2. The solid was filtered off, and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography (0-80% EtOAc/hexanes) to give the title compound as a pale-yellow solid (50 mg, 96%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.82 (m, 1H), 7.72 (m, 1H), 7.57-7.43 (m, 5H), 7.20 (d, 1H), 6.75 (d, 1H), 6.66 (s, 1H), 3.77 (m, 4H), 3.66 (s, 2H), 3.07 (s, 3H), 2.60 (m, 4H). MS(ES): 514 [M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by flash chromatography (0-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-34fae5d201114efab49a18b15d7e7dc6
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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