HCID 69669258, compound → HCID 69669262, compound

HRID 1470567Notes

Reaction equation

HRID 1470567 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1[CH:28]=[CH:27][C:6]([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([NH:19]C(=O)OC(C)(C)C)[CH:13]=[CH:12]3)=[O:8])=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O.ClCCl>[NH2:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:7]([C:6]1[CH:27]=[CH:28][C:3]([N:2]([CH3:29])[CH3:1])=[CH:4][CH:5]=1)=[O:8])[CH:18]=[CH:17]2

Participants

4

Reactant 1

HCID 69669258HCID 69669258, compound

Product 1

HCID 69669262HCID 69669262, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The compound 9 (70 mg, 0.18 mmol) was stirred in 10% TFA in dichloromethane (10 mL) at room temperature for 1 hour and extracted with ethyl acetate with aqueous NaHCO3. The organic layer was dried over Na2SO4, and the filtrate was concentrated to give intermediate D (50 mg, 96%). 1H-NMR (CD3OD) 8.02 (s, 1H), 7.59-7.78 (m, 5H), 7.00-7.07 (m, 2H), 6.80 (m, 3H), 3.09 (s, 6H) ppm; ESI-MS m/z calcd for C19H18N2O: 290.3590. found 291.1821 [M+1].

Workup

  1. extractionextracted with ethyl acetate with aqueous NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1efd6f8a5f0c41a5acf8d9a5bf2fb862
Source dataset
uspto-grants-2015_04
Patent number
US09006458B2

Reaction notes

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