Trifluoroacetic acid → HCID 58116820, compound

HRID 38571Notes

Reaction equation

HRID 38571 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][N:21]([C:23](=[O:40])/[CH:24]=[CH:25]/[CH2:26][N:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)[CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][N:21]([C:23](=[O:40])/[CH:24]=[CH:25]/[CH2:26][N:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)[CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58116813HCID 58116813, compound

Product 1

HCID 58116820HCID 58116820, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[(2E)-4-{4-[(3-chloro-4-fluorophenyl)amino]-5,8-dihydropyrido-[4′,3′:4,5]thieno[2,3-d]pyrimidin-7(6H)-yl}-4-oxobut-2-en-1-yl]piperazine-1-carboxylate from Example 3 (150 mg, 0.255 mmol) in dichloromethane (15 mL) was added TFA (1.0 mL, 13 mmol), and the mixture was stirred at rt for 5 h. The solvent was removed in vacuo. 1 M aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated. The residue was crystallized from dichloromethane/diethyl ether to yield 108 mg (87%) of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. addition1 M aqueous sodium hydroxide solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-94ec37f476d14342b8dd5d19b3d6f538
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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