Water → Lurosetron

HRID 2081231Notes

Reaction equation

HRID 2081231 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=[O:9])C=1Cl.[F:15][C:16]1[C:24]2[N:23]([CH3:25])[C:22]3[CH2:26][CH2:27][N:28]([CH2:30][C:31]4[N:32]=[CH:33][NH:34][C:35]=4[CH3:36])[CH2:29][C:21]=3[C:20]=2[CH:19]=[CH:18][CH:17]=1.O>C1COCC1>[F:15][C:16]1[C:24]2[N:23]([CH3:25])[C:22]3[CH2:26][CH2:27][N:28]([CH2:30][C:31]4[N:32]=[CH:33][NH:34][C:35]=4[CH3:36])[C:29](=[O:9])[C:21]=3[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 197992756-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indole

Product 1

HCID 172999LurosetronYield 20.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (133 mg) in THF (4 ml) was added dropwise to a stirred solution of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1Hpyrido[4,3-b]indole (70 mg) in THF (12 ml) at -10° under nitrogen, and stirring was continued for 4 h. Water (20 ml) was then added, and the resulting solution was left to stand overnight. Excess THF was removed in vacuo, and the resultant aqueous solution was extracted with ethyl acetate (3×50 ml). The combined, dried organic extracts were adsorbed onto silica and purified by FCC eluting with System A (100:10:1) to give the title compound (15 mg), m.p. 231.5°-233°.

Workup

  1. waitthe resulting solution was left
  2. waitto stand overnight
  3. customExcess THF was removed in vacuo
  4. extractionthe resultant aqueous solution was extracted with ethyl acetate (3×50 ml)
  5. custompurified by FCC
  6. washeluting with System A (100:10:1)

Sources & evidence

ORD record
ord-00e24d1acfc5431d932fdce8b9447578
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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