Trifluoroacetic acid → 2-methy-N1-[6-(spiro[1-benzofuran-3,1'-cyclopropan]-4-yloxy)-3-pyridinyl]alaninamide

HRID 1023636Notes

Reaction equation

HRID 1023636 reaction equation
[CH3:1][C:2]([NH:25]C(=O)OC(C)(C)C)([CH3:24])[C:3](=[O:23])[NH:4][C:5]1[CH:6]=[N:7][C:8]([O:11][C:12]2[C:17]3[C:18]4([CH2:21][O:22][C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH2:20][CH2:19]4)=[CH:9][CH:10]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:24][C:2]([C:3]([NH:4][C:5]1[CH:6]=[N:7][C:8]([O:11][C:12]2[C:17]3[C:18]4([CH2:21][O:22][C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH2:20][CH2:19]4)=[CH:9][CH:10]=1)=[O:23])([CH3:1])[NH2:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 683224941,1-Dimethylethyl (1,1-dimethyl-2-oxo-2-{[6-(spiro[1-benzofuran-3,1'-cyclopropan]-4-yloxy)-3-pyridinyl]amino}ethyl)carbamate2×

Product 1

HCID 672355492-methy-N1-[6-(spiro[1-benzofuran-3,1'-cyclopropan]-4-yloxy)-3-pyridinyl]alaninamideYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl (1,1-dimethyl-2-oxo-2-{[6-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)-3-pyridinyl]amino}ethyl)carbamate (Reference Intermediate 219, 50 mg) in dry dichloromethane (4 mL) at 0° C. TFA (1 ml, 12.98 mmol) was slowly added and the reaction mixture was stirred for 2 hours at the same temperature. The reaction was diluted with dichloromethane (10 ml) and an aqueous saturated solution of NaHCO3 was added while the pH was allowed to reach ˜8. Two phases were separated and the organic layer was dried over sodium sulphate, filtered and evaporated affording the title compound (35 mg) as a colourless oil.

Workup

  1. customat 0° C
  2. customTwo phases were separated
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-81cc9066a0b1480ea4739f14ccb59e69
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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