Trifluoroacetic acid → HCID 66849464, compound

HRID 1046436Notes

Reaction equation

HRID 1046436 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]#[C:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[NH2:10])=[O:4].[C:17]([OH:23])([C:19](F)(F)F)=O.C([SiH]([CH2:29][CH3:30])CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]#[C:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[NH:10][CH:30]1[CH2:29][CH2:9][CH:8]([O:23][CH:17]2[CH2:19][CH2:3][O:2][CH2:1]2)[CH2:7][CH2:11]1)=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 24989346Methyl 3-amino-5-(3,3-dimethylbut-1-yn-1-yl)thiophene-2-carboxylate

Product 1

HCID 66849464HCID 66849464, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-amino-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (2.62 g, 11.06 mmol), 4-(tetrahydro-furan-3S-yloxy)-cyclohexanone (1.7 g, 9.22 mmol), TFA (2.84 mL, 36.9 mmol) and triethylsilane (2.94 mL, 18.44 mmol) in CH2Cl2 (15 mL) was stirred for 24 h at room temperature. The reaction was concentrated in vacuo to remove volatiles and the crude oil was dissolved in toluene (50 mL) and concentrated (repeat) to give a yellow solid. The crude solid was purified by column chromatography (hexane/ethylacetate) to give 5-(3,3-dimethyl-but-1-ynyl)-3-[4-(tetrahydro-furan-3-yloxy)-cyclohexylamino]-thiophene-2-carboxylic acid methyl ester (1.35 g, 3.33 mmol) as a single isomer.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto remove volatiles
  3. dissolutionthe crude oil was dissolved in toluene (50 mL)
  4. concentrationconcentrated (repeat)
  5. customto give a yellow solid
  6. customThe crude solid was purified by column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-157cb12c641341df8aac8bc2f81d6d6a
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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