Trifluoroacetic anhydride → HCID 21062819, compound

HRID 1242807Notes

Reaction equation

HRID 1242807 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:25]=[C:24]([CH2:26][CH3:27])[S:23][C:16]=3[N:17]=[C:18]([C:20](=O)[NH2:21])[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]3[CH:25]=[C:24]([CH2:26][CH3:27])[S:23][C:16]=3[N:17]=[C:18]([C:20]#[N:21])[N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 21062821HCID 21062821, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 21062819HCID 21062819, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Carbamoyl-6-ethyl-thieno[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (28.2 mg) was dissolved in methylene chloride (1.00 mL) and diisopropyl-ethylamine (0.13 mL) and trifluroacetic anhydride (40.7 μL) was added. After stirring at room temperature for 2.5 hours, the product was isolated from silica gel chromatography (15% to 35% ethyl acetate/hexane over 40 minutes). Yield=46%, ES-MS: (M+H)+ 374.

Sources & evidence

ORD record
ord-5dc54d1d9beb4d148936fe29f2e49b9c
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

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