Formamide → Alosetron

HRID 2379161Notes

Reaction equation

HRID 2379161 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[O:22])[N:12]([CH2:15][C:16]3O[CH:19]=[N:18][C:17]=3[CH3:21])[CH2:13][CH2:14][C:3]1=2.C([NH2:25])=O>O>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[O:22])[N:12]([CH2:15][C:16]3[N:25]=[CH:19][NH:18][C:17]=3[CH3:21])[CH2:13][CH2:14][C:3]1=2

Participants

4

Reactant 2

HCID 713FormamideHCID 189577262,3,4,5-tetrahydro-5-methyl-2-[(4-methyloxazol-5-yl)methyl]-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 2099Alosetron

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,3,4,5-tetrahydro-5-methyl-2-[(4-methyloxazol-5-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (100 mg) in formamide (20 ml) was heated at 180° for 24 h. The mixture was then cooled, diluted with water (100 ml) and extracted with dichloromethane (3×100 ml). The combined organic extracts were concentrated in vacuo and the residue was purified by FCC eluting with System A (100:8:1) to give the title compound (40 mg) as a solid. The 1H-n.m.r. and t.l.c. data for this material were consistent with those obtained for the product of Example 20.

Workup

  1. temperaturewas heated at 180° for 24 h
  2. temperatureThe mixture was then cooled
  3. extractionextracted with dichloromethane (3×100 ml)
  4. concentrationThe combined organic extracts were concentrated in vacuo
  5. customthe residue was purified by FCC
  6. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-04f85528fdcc4399a107bf857b31fd1d
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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