Formamidine acetate → HCID 58116975, compound

HRID 38559Notes

Reaction equation

HRID 38559 reaction equation
[NH2:1][C:2]1[S:10][C:9]2[CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5][C:4]=2[C:3]=1[C:18]([O:20]CC)=O.C(O)(=O)C.[CH:27](N)=[NH:28]>CN(C=O)C>[O:20]=[C:18]1[NH:28][CH:27]=[N:1][C:2]2[S:10][C:9]3[CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:5][C:4]=3[C:3]1=2

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 58116861HCID 58116861, compound

Product 1

HCID 58116975HCID 58116975, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-tert-Butyl 3-ethyl 2-amino-6,7-dihydrothieno[3,2-c]pyridine-3,5(4H)-dicarboxylate from Example 73A (780 mg, 2.39 mmol) was dissolved in DMF (8 mL), and formamidine acetate (373 mg, 3.58 mmol) was added. The reaction mixture was heated to 100° C. overnight. The solvent was then removed in vacuo, and the residue was dissolved in ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and the solvent was removed in vacuo. The residue was triturated with tert-butyl methyl ether, and the precipitate was collected by suction filtration to yield 414 mg (56%) of the title compound as a tan solid. The mother liquor was concentrated and purified by preparative HPLC to yield a second batch of 36 mg (5%).

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was triturated with tert-butyl methyl ether
  7. filtrationthe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-f8657fd21b0542e5a8bccdc0a05a4571
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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