Water → HCID 73855058, compound

HRID 2121970Notes

Reaction equation

HRID 2121970 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:24][C:25]1[CH:26]=[C:27]([NH:34]C(=O)C(F)(F)F)[CH:28]=[CH:29][C:30]=1[NH:31][CH2:32][CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[NH2:34][C:27]1[CH:28]=[CH:29][C:30]([NH:31][CH2:32][CH3:33])=[C:25]([N:24]=[C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:12](=[O:13])[C:11](=[C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[S:15]3)[S:10]2)[CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 73855025HCID 73855025, compound

Product 1

HCID 73855058HCID 73855058, compoundYield 1.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To the product of Example 138 (0.15 g, 0.26 mmol) in MeOH (30 mL) was added H2O (6 mL) and fine mesh K2CO3 (0.30 g, 1.5 mmol), and the solution was stirred 24 h at 55° C. The reaction mixture was cooled, diluted with EtOAc (30 mL), washed with H2O (20 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by reverse-phase HPLC (C18 column), eluting with 0.05% TFA in MeCN—H2O (1:9 to 9:1) to provide the title compound (2 mg). MS(ESI): 488 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with H2O (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by reverse-phase HPLC (C18 column)
  7. washeluting with 0.05% TFA in MeCN—H2O (1:9 to 9:1)

Sources & evidence

ORD record
ord-29544107f73d499bacf3e91ef5efc02d
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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