Trifluoroacetic acid → HCID 90370057, compound

HRID 2176028Notes

Reaction equation

HRID 2176028 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:22]3[CH2:23][CH2:24][CH2:25][CH2:26][C:21]=3[S:20][C:19]=2[NH:27][C:28](=[O:42])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH:30]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O.CC1C=C(C)C(C)=C(C)C=1C>>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]2[C:22]3[CH2:23][CH2:24][CH2:25][CH2:26][C:21]=3[S:20][C:19]=2[NH:27][C:28](=[O:42])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[CH:30]=2)=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12784PentamethylbenzeneHCID 90370174HCID 90370174, compound

Product 1

HCID 90370057HCID 90370057, compoundYield 100%

Procedure

To a mixture of 200 mg of N-[4-(benzyloxy)phenyl]-2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide and 6.0 mL of TFA was added 255 mg of 1,2,3,4,5-pentamethylbenzene, followed by stirring overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added thereto, followed by extraction using ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (3% methanol/chloroform), thereby obtaining 169 mg of N-(4-hydroxyphenyl)-2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additiona saturated aqueous sodium hydrogen carbonate solution were added
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-07a56a56a43f4bf29f9fa4b4c07ba2d4
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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