HCID 22728615, compound → HCID 22728606, compound

HRID 2084989Notes

Reaction equation

HRID 2084989 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19](=[O:32])[NH:20][C:21](=[O:31])[C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[CH:13][CH:12]=1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl.C(OCC)(=O)C>[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]2[C:19](=[O:32])[NH:20][C:21](=[O:31])[C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 22728615HCID 22728615, compound

Product 1

HCID 22728606HCID 22728606, compound

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[4-[2-(t-butoxycarbonylamino)ethyl]phenylamino]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione (0.060 g. 0.13 mmol) and trifluoroacetic acid (4 drops) in dry DCM (5 mL) was stirred for 18 hours at room temperature. The suspension was diluted with ethyl acetate (10 mL), poured onto sodium bicarbonate (20 mL) and extracted with ethyl acetate (3×10 mL). The combined organic solutions were washed with brine, dried with magnesium sulfate, evaporated and the residue triturated with a mixture of hexane-dichloromethane (95:5 v/v) to afford the tide compound as an orange solid.

Workup

  1. additionpoured onto sodium bicarbonate (20 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customthe residue triturated with a mixture of hexane-dichloromethane (95:5 v/v)

Sources & evidence

ORD record
ord-513fb49a54a74ee2ba2e3edfd5015cc2
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

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