Diisopropylethylamine → HCID 178437207, compound

HRID 706042Notes

Reaction equation

HRID 706042 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].[CH2:21]([C:23]1[C:24](=[O:30])[NH:25][C:26](=[S:29])[NH:27][CH:28]=1)[CH3:22].CCN(C(C)C)C(C)C>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:29][C:26]3[NH:27][CH:28]=[C:23]([CH2:21][CH3:22])[C:24](=[O:30])[N:25]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 30020425-Ethyl-2-thiouracilHCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl ether

Product 1

HCID 178437207HCID 178437207, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 1-chloro-4-{[4-(chloromethyl)phenyl]oxy}-2-(trifluoromethyl)benzene (65 mg, 0.202 mmol), 5-ethyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (47.4 mg, 0.304 mmol) and DIPEA (0.163 mL, 0.933 mmol) in DCE (3.0 mL) was sealed in a vessel and stirred at room temperature for 5 min, then was heated with a microwave condition at 80° C. for 30 min. After cooling, the reaction was quenched with water, extracted with EA, the combined organic layers were dried with sodium sulfate, concentrated, and purified via MDAP to afford the title compound (41 mg, 45.9% yield). LCMS: rt=3.94 min, [M+H+]=441

Workup

  1. customwas sealed in a vessel
  2. temperaturewas heated with a microwave condition at 80° C. for 30 min
  3. temperatureAfter cooling
  4. customthe reaction was quenched with water
  5. extractionextracted with EA
  6. dry with materialthe combined organic layers were dried with sodium sulfate
  7. concentrationconcentrated
  8. custompurified via MDAP

Sources & evidence

ORD record
ord-3d9eb5c7b0484a23b3e16c5aa461fff3
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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