Dichloromethane → HCID 10158342, compound

HRID 1634087Notes

Reaction equation

HRID 1634087 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]2)=[CH:4][CH:3]=1.C(Cl)Cl.C(N(C(C)C)CC)(C)C.[N:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C(OCC)(=O)C>[F:18][C:17]([F:20])([F:19])[C:10]1[CH:11]=[C:12]([C:13]([F:14])([F:15])[F:16])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:39]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[O:40])=[CH:7][CH:6]=2)[N:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 10158342HCID 10158342, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4′-aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.300 g, 1.02 mmol) in of methylene chloride (5 mL) was added diisopropylethyl amine (0.18 mL, 1.0 mmol) followed by 4-morpholine carbonylchloride (0.11 mL, 1.0 mmol). The mixture was stirred at rt for 6 days, and diluted with ethyl acetate. It was then washed twice with water, dried over sodium sulfate and evaporated. Chromatography of the residue over silica gel (50% EtOAc/hexanes) gave the above-named compound (0.080 g, 19.6%) as a white solid: mp 185-186° C. NMR (CDCl3) δ 7.56 (2H, d), 7.44 (2H, d), 7.07 (1H, s), 6.51 (1H, s), 3.79 (4H, m), 3.54 (4H, m).

Workup

  1. washIt was then washed twice with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-471685f917b74941a5d78d32e7829b37
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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