N-Iodosuccinimide → HCID 57526814, compound

HRID 1452644Notes

Reaction equation

HRID 1452644 reaction equation
[C:1]([O:5][C:6]([N:8]([C:34]1[CH:43]=[CH:42][C:37]2[N:38]=[C:39]([CH3:41])[S:40][C:36]=2[CH:35]=1)[C:9]1[N:20]2[C:16](=[CH:17][CH:18]=[N:19]2)[N:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][N:13]2[C@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:44]N1C(=O)CCC1=O>C1COCC1>[I:44][C:17]1[CH:18]=[N:19][N:20]2[C:16]=1[N:15]=[C:14]1[C:10]([CH2:11][CH2:12][N:13]1[C@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)=[C:9]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:34]1[CH:43]=[CH:42][C:37]2[N:38]=[C:39]([CH3:41])[S:40][C:36]=2[CH:35]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 57526793HCID 57526793, compound

Product 1

HCID 57526814HCID 57526814, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (1.5 mL) of tert-butyl (S)-3-[8-{tert-butoxycarbonyl-(2-methylbenzothiazol-6-yl)amino}-6,7-dihydro-1,4,5,8a-tetraaza-s-indacen-5-yl]piperidine-1-carboxylate (97.6 mg, 0.161 mmol), N-iodosuccinimide (43.5 mg, 0.193 mmol) was added at room temperature and the mixture was stirred for 3 hr. After the reaction, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was removed under reduced pressure and the residue was purified with column chromatography (30% ethyl acetate-hexane) to obtain the title compound (109.7 mg).

Workup

  1. customAfter the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialbrine and dried over sodium sulfate
  5. filtrationAfter the sodium sulfate was filtered off
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified with column chromatography (30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c53dc4231d65409ea2de957bc9ba5385
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

Loading…