Sodium Hydroxide → tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 2365404Notes

Reaction equation

HRID 2365404 reaction equation
[O:1]=[C:2]1[CH2:7][N:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4][N:3]1[C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36][CH2:35][C:21]=3[N:22](S(C3C=CC(C)=CC=3)(=O)=O)[C:23]=2[CH:24]=1.[OH-].[Na+]>CO.C(Cl)Cl>[O:1]=[C:2]1[CH2:7][N:6]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:5][CH2:4][N:3]1[C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36][CH2:35][C:21]=3[NH:22][C:23]=2[CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67986824tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-5-tosyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 67986821tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 47.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-5-tosyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (450 mg, 0.716 mmol) and NaOH (800 mg, 20 mmol) were stirred in MeOH/CH2Cl2 (5 mL/5 mL) for 16 h. The mixture was partitioned between CH2Cl2 and water and the organic layer removed, dried and concentrated. The residue was purified by column chromatography (40 g ISCO column eluting with methylene chloride and a 10:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 90% methylene chloride) to provide the title compound (160 mg, 47%) as a white powder: 1H NMR (500 MHz, DMSO-d6) δ 10.95 (s, 1H), 7.35 (d, J=8.2 Hz, 1H), 7.32-7.25 (m, 4H), 7.22-7.17 (m, 2H), 6.88-6.86 (dd, J=8.3, 1.8 Hz, 1H), 4.51 (s, 2H), 3.69 (t, J=5.6 Hz, 2H), 3.64 (t, J=5.3 Hz, 2H), 3.33 (m, 2H), 2.88-2.83 (m, 2H), 2.83-2.74 (m, 4H), 2.69-2.63 (m, 2H), 1.43 (s, 9H).

Workup

  1. customThe mixture was partitioned between CH2Cl2 and water
  2. customthe organic layer removed
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (40 g ISCO column
  6. washeluting with methylene chloride

Sources & evidence

ORD record
ord-ca58f1ef932347fd9da08df2cfdb9864
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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