Potassium Carbonate → HCID 22605718, compound

HRID 2307300Notes

Reaction equation

HRID 2307300 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8](=[O:35])[C:9]([C:20]([C:22]2[CH:26]=[C:25]([CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[S:24][C:23]=2Cl)=[O:21])=[CH:10][NH:11][CH2:12][CH2:13]N2CCOCC2)=[CH:4][CH:3]=1.[C:38]([O-:41])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:9]2[C:20](=[O:21])[C:22]3[CH:26]=[C:25]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[S:24][C:23]=3[N:11]([CH2:12][CH2:13][CH:6]3[NH:7][CH2:8][CH2:38][O:41][CH2:5]3)[CH:10]=2)=[O:35])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178522951HCID 178522951, compound

Product 1

HCID 22605718HCID 22605718, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(4-chlorobenzyl)-2-((2-chloro-5-(morpholin-4-ylmethyl)thien-3-yl)carbonyl)-3-((2-morpholin-4-ylethyl)amino)acrylamide (Preparation 6, 4.3 g) and K2CO3 (1.6 g) in DMF (75 mL) is stirred at 100° C. for 5 h. The mixture is allowed to cool to room temperature and is concentrated in vacuo. The crude product is triturated with EtOAc and filtered to afford 1.4 g of the title compound as a yellow solid Physical characteristics. 1H NMR (300 MHz, DMSO-d6) δ 10.57, 8.71, 7.42-7.32, 4.55, 4.37, 3.74, 3.59, 3.50, 2.73, 2.44; MS (ESI+) m/z 531 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. concentrationis concentrated in vacuo
  3. customThe crude product is triturated with EtOAc
  4. filtrationfiltered

Sources & evidence

ORD record
ord-03504aa9309141009a51783b0342e6fb
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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