Alosetron → Phenylmethyl 5-methyl-4-[(2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido[4,3-b]indol-2yl)methyl]-1H-imidazole-1-carboxylate

HRID 2379149Notes

Reaction equation

HRID 2379149 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][N:13]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:22](=[O:33])[N:23]([CH2:26][C:27]3[N:28]=[CH:29][NH:30][C:31]=3[CH3:32])[CH2:24][CH2:25][C:14]1=2.C(N(CC)CC)C>ClCCl>[CH3:32][C:31]1[N:30]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH:29]=[N:28][C:27]=1[CH2:26][N:23]1[CH2:24][CH2:25][C:14]2[N:13]([CH3:12])[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]=2[C:22]1=[O:33]

Participants

5

Reactant 3

HCID 2099AlosetronHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 18957736Phenylmethyl 5-methyl-4-[(2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido[4,3-b]indol-2yl)methyl]-1H-imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (0.28 ml) in dichloromethane (10 ml) was added to a stirred solution of 2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1one (294 mg) and triethylamine (0.4 ml) in dichloromethane (30 ml) at 20° under nitrogen, and the mixture was stirred overnight. It was then concentrated onto FCC silica and purified by FCC eluting with System A (200:8:1) to give the title compound (62 mg), t.l.c. (System A, 100:8:1) Rf 0.50.

Workup

  1. concentrationIt was then concentrated onto FCC silica
  2. custompurified by FCC
  3. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-1b35d055b72b4f71a75ee5b6cd41bd88
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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