Trifluoroacetic acid → HCID 10565105, compound

HRID 729235Notes

Reaction equation

HRID 729235 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH2:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[F:15][C:16]([F:21])([F:20])[C:17](O)=[O:18].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH:14][C:17](=[O:18])[C:16]([F:21])([F:20])[F:15])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 128113521-(7-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

Product 1

HCID 10565105HCID 10565105, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14 (3.0 g, 17 mmol), trifluoroacetic acid (2 ml, 28 mmol) and trifluoroacetic anhydride (4 ml, 28 mmol) in CH2Cl2 is refluxed for 15 minutes, cooled, and the mixture is poured onto ice, extracted twice with CH2Cl2 and evaporated. The mixture is chromatographed on silica gel to give 4.5 g of compound 15 (94% yield). 1H NMR [300 MHz, (CD3)2SO], a 3:2 mixture of amide conformers doubling most signals, δ 11.24 (0.8H, s, NH), 11.21 (1.2H, s, NH), 7.55-7.40 (2H, m, H5.8), 7.22 (0.6H, s, H-6), 7.20 (0.4H, s, H-6), 4.64 (0.8H, s, ArCH2N), 4.57 (1.2H, s, ArCH2N), 3.65 (2H, t, ArCH2CH2N), 2.84 (1.2H, t, ArCH2CH2N), 2.73 (0.8H, t, ArCH2CH2N), 2.06 (1.2H, s, COCH3), 2.05 (1.8H, s COCH3).

Workup

  1. temperaturecooled
  2. additionthe mixture is poured onto ice
  3. extractionextracted twice with CH2Cl2
  4. customevaporated
  5. customThe mixture is chromatographed on silica gel

Sources & evidence

ORD record
ord-19f15aad123f41cfadea4680d0d2d908
Source dataset
uspto-grants-2009_09
Patent number
US07582616B2

Reaction notes

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