Chlorosuccinimide → HCID 67228421, compound

HRID 1848923Notes

Reaction equation

HRID 1848923 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][C:13]2[CH:14]=[N:15][C:16]([NH:19][CH3:20])=[CH:17][CH:18]=2)[CH:3]=1.[Cl:21]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Cl:21][C:17]1[CH:18]=[C:13]([O:12][C:4]2[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[CH:14]=[N:15][C:16]=1[NH:19][CH3:20]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 67227548HCID 67227548, compound

Product 1

HCID 67228421HCID 67228421, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of EXAMPLE 377D (0.450 g) and N-chlorosuccinimide (0.239 g) was stirred together in N,N-dimethylformamide (10 mL) at room temperature. The reaction was stirred for 48 hours, diluted with ethyl acetate (100 mL), washed with water (2×50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 40 g) eluting with a gradient of 5-30% ethyl acetate/hexanes over 30 minutes (flow=40 ml/min) provided the title compound.

Workup

  1. washwashed with water (2×50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washSilica gel chromatography (Reveleris 40 g) eluting with a gradient of 5-30% ethyl acetate/hexanes over 30 minutes (flow=40 ml/min)

Sources & evidence

ORD record
ord-e8b15d81ba404c8686269497c12c455a
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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