Potassium Carbonate → HCID 59753823, compound

HRID 1819618Notes

Reaction equation

HRID 1819618 reaction equation
CC1C(C[N:8]2[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][C:24]([OH:26])=[O:25])[C:15]=3[CH3:27])([CH3:13])[C:11]3[CH:28]=[CH:29][CH:30]=[CH:31][C:10]=3[S:9]2(=[O:33])=[O:32])=C(C)ON=1.C([O-])([O-])=O.[K+].[K+].[F:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[CH2:45]Br>CN(C=O)C.CCOC(C)=O>[F:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[CH2:45][N:8]1[C:12]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]([OH:26])=[O:25])[C:15]=2[CH3:27])([CH3:13])[C:11]2[CH:28]=[CH:29][CH:30]=[CH:31][C:10]=2[S:9]1(=[O:33])=[O:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 11605389HCID 11605389, compound

Product 1

HCID 59753823HCID 59753823, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

The product of example 65, step a) (50 mg, 0.12 mmol) was dissolved in 2 mL DMF and treated with K2CO3 (32 mg, 0.23 mmol) and 3-fluoro-benzylbromide (43 mg, 0.23 mmol). After heating to 75° C. for 2 h, the reaction was cooled, diluted with EtOAc, and washed 3× H2O. The organic solution was concentrated and treated with 3 mL TFA for 2 h at rt. The reaction was concentrated and the title compound was isolated by preparative LCMS to give the title compound. MS: ESI (negative): 477.5 (M−H).

Workup

  1. temperaturethe reaction was cooled
  2. washwashed 3× H2O
  3. concentrationThe organic solution was concentrated
  4. additiontreated with 3 mL TFA for 2 h at rt
  5. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-74e5775ad3154697afe6e2f7c6258bc9
Source dataset
uspto-grants-2009_10
Patent number
US07601749B2

Reaction notes

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