Formamide → Lurosetron

HRID 2081229Notes

Reaction equation

HRID 2081229 reaction equation
[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4O[CH:21]=[N:20][C:19]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([NH2:26])=O>O>[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[N:26]=[CH:21][NH:20][C:19]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 157125256-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(4-methyloxazol-5-yl)methyl]-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 172999Lurosetron

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(4-methyloxazol-5-yl) methyl]-1H-pyrido[4,3-b]indol-1-one (180 mg) and formamide (20 ml) was heated at 180° for 18 h. The solution was then cooled (0°), diluted with water (100 ml) and extracted with dichloromethane (3×100 ml). The combined extracts were concentrated in vacuo and purified by FCC eluting with System A (100:8:1) to give the title compound (110 mg), m.p. 230°-233°.

Workup

  1. temperaturewas heated at 180° for 18 h
  2. temperatureThe solution was then cooled (0°)
  3. extractionextracted with dichloromethane (3×100 ml)
  4. concentrationThe combined extracts were concentrated in vacuo
  5. custompurified by FCC
  6. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-f0679900ae8d44b29c003a0fa58056f1
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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