Diisopropylethylamine → HCID 86645384, compound

HRID 222549Notes

Reaction equation

HRID 222549 reaction equation
CCN(C(C)C)C(C)C.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][C:16](Cl)=[O:17].[Cl:19][C:20]1[C:29]([NH2:30])=[CH:28][C:27]2[C:22](=[CH:23][C:24]([C:31]([F:34])([F:33])[F:32])=[CH:25][CH:26]=2)[N:21]=1.CCCCCC.CC(=O)OCC>C(Cl)Cl>[Cl:19][C:20]1[C:29]([NH:30][C:16](=[O:17])[CH2:15][C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)=[CH:28][C:27]2[C:22](=[CH:23][C:24]([C:31]([F:32])([F:34])[F:33])=[CH:25][CH:26]=2)[N:21]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 21226206Ethyl acetate hexaneHCID 86645382HCID 86645382, compound

Product 1

HCID 86645384HCID 86645384, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

373 μl (4 mmol) of DIPEA and 385 mg (2.4 mmol) of 2-(thiophen-2-yl)acetyl chloride were added in succession at 0° C. to a solution of 493 mg (2 mmol) of 2-chloro-7-(trifluoromethyl)quinolin-3-amine (VC05) in DCM (14 ml). After stirring for 16 h at RT, the mixture was diluted with DCM. It was then washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 19:1) of the residue yielded 321 mg (0.87 mmol, 44%) of N-(2-chloro-7-(trifluoromethyl)quinolin-3-yl)-2-(thiophen-2-yl)acetamide.

Workup

  1. washIt was then washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9166df34b5c34edc9f8a4fb167dddc46
Source dataset
uspto-grants-2012_06
Patent number
US08207342B2

Reaction notes

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