Triethylamine → Phenylmethyl 4-[(6-fluoro-2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido [4,3-b]indol-2-yl)methyl]-5-methyl-1H-imidazole-1-carboxylate

HRID 2081222Notes

Reaction equation

HRID 2081222 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].[F:12][C:13]1[C:21]2[N:20]([CH3:22])[C:19]3[CH2:23][CH2:24][N:25]([CH2:28][C:29]4[N:30]=[CH:31][NH:32][C:33]=4[CH3:34])[C:26](=[O:27])[C:18]=3[C:17]=2[CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[OH-].[Na+]>ClCCl>[F:12][C:13]1[C:21]2[N:20]([CH3:22])[C:19]3[CH2:23][CH2:24][N:25]([CH2:28][C:29]4[N:30]=[CH:31][N:32]([C:2]([O:4][CH2:5][C:6]5[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=5)=[O:3])[C:33]=4[CH3:34])[C:26](=[O:27])[C:18]=3[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 172999Lurosetron

Product 1

HCID 15712526Phenylmethyl 4-[(6-fluoro-2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido [4,3-b]indol-2-yl)methyl]-5-methyl-1H-imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (0.47 ml) in dichloromethane (1 ml) was added to a stirred solution of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl -1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (496 mg) and triethylamine (0.67 ml) in dry dichloromethane (50 ml) at 20° under nitrogen, and the mixture was stirred overnight. The cooled reaction mixture was then added to 2N sodium hydroxide (100 ml) and extracted with dichloromethane (2×100 ml). The combined, dried organic extracts were adsorbed onto silica and purified by FCC eluting with System A (200:8:1) to give the title compound (442 mg) as a solid. A sample was recrystallised from hot ethyl acetate, and the resultant solid was triturated with ether to give a crystalline solid, m.p. 126°-128°.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with dichloromethane (2×100 ml)
  3. custompurified by FCC
  4. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-dc74b9c5167543b4a7ed76b4ee227135
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

Loading…