Chlorosuccinimide → HCID 25106870, compound

HRID 2423276Notes

Reaction equation

HRID 2423276 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=2[O:33][CH3:34])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:35])[NH:17]2)(=[O:11])=[O:10].[Cl:36]N1C(=O)CCC1=O>CN(C)C=O>[Cl:36][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:21]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=3[O:33][CH3:34])[C:13]=2[NH:12][S:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])(=[O:11])=[O:10])[NH:17][C:16]=1[CH3:35]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 25106869HCID 25106869, compound

Product 1

HCID 25106870HCID 25106870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A room temperature solution of 1 (14 mg, 0.026 mmol) and N-chlorosuccinimide (4 mg, 0.029 mmol) dissolved in N,N-dimethylformamide (1 mL) was stirred for 40 min., after which time HPLC indicated no 1 remained. The reaction was partitioned between ethyl acetate and 10% sodium thiosulfate aqueous solution. The organic separation was washed twice with water then brine. The organic layer was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a colorless solid. The product was isolated by semi-preparative reversed phase HPLC to afford a colorless solid. LC-MS ESI (neg.) m/z: 567.1 (M−H). 1H NMR (400 MHz) (d6-DMSO) δ 11.41 (s, 1H); 9.66 (br s, 1H); 7.64 (d, J=8 Hz, 1H); 7.52 (s, 1H); 7.18 (d, J=8.0 Hz, 1H); 6.86 (s, 1H); 6.61 (d, J=8.0 Hz, 1H); 6.35 (d, J=8.0 Hz, 1H); 6.23 (d, J=8.0 Hz, 1H); 3.66 (s, 3H); 3.51 (s, 2H); 2.38 (s, 3H) ppm.

Workup

  1. customThe reaction was partitioned between ethyl acetate and 10% sodium thiosulfate aqueous solution
  2. customThe organic separation
  3. washwas washed twice with water
  4. stirringThe organic layer was stirred over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  7. customto afford a colorless solid
  8. customThe product was isolated by semi-preparative reversed phase HPLC
  9. customto afford a colorless solid

Sources & evidence

ORD record
ord-ff00a4fdf18a4b5694bf729394fcb597
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

Loading…