Chlorosuccinimide → HCID 42606319, compound

HRID 910162Notes

Reaction equation

HRID 910162 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:18]([C:19]([NH:21][O:22][CH2:23][CH2:24][OH:25])=[O:20])=[C:17]2[N:13]([CH2:14][CH2:15][CH2:16]2)[C:12](=[O:26])[CH:11]=1.[Cl:27]N1C(=O)CCC1=O>CN(C=O)C>[Cl:27][C:11]1[C:12](=[O:26])[N:13]2[C:17](=[C:18]([C:19]([NH:21][O:22][CH2:23][CH2:24][OH:25])=[O:20])[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])[CH2:16][CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 42606318HCID 42606318, compound

Product 1

HCID 42606319HCID 42606319, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Example 9 (22 mg, 0.047 mmol) was dissolved in DMF (2 mL) and N-chlorosuccinimide (8 mg, 0.056 mmol) was added and the reaction was allowed to stir at r.t. for 4 hr. The mixture was concentrated in vacuo and purified by preparative HPLC (25/35 water/acetonitrile) to give 5 mg (21%) of the title compound. 1H NMR (400 MHz, MeOD): δ 7.98 (s, 1H), 7.50 (dd, 1H, J=10.0, 1.6 Hz), 7.44 (m, 1H), 6.87 (t, 1H, J=8.6 Hz), 4.17 (t, 2H, J=7.8 Hz), 3.59 (m, 2H), 3.34 (m, 2H), 3.17 (t, 2H, J=7.4 Hz), 2.43 (m, 2H). MS (ES) [m+H] calc'd for C17H16 ClFIN3O4, 508. found 508.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by preparative HPLC (25/35 water/acetonitrile)

Sources & evidence

ORD record
ord-4c29691a781b4f8f85e70dd98d08b7ae
Source dataset
uspto-grants-2011_09
Patent number
US08022057B2

Reaction notes

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