tert-Butyl methyl ether → 1-(1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide maleate

HRID 495011Notes

Reaction equation

HRID 495011 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:35])([CH3:34])[O:10]2)=[CH:5][CH:4]=1.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].COC(C)(C)C>O1CCCC1>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:34])([CH3:35])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 444266Maleic AcidHCID 11677552E-2110 free base

Product 1

HCID 688561021-(1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide maleateYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-{1-[2-(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide (105 mg) was dissolved in tetrahydrofuran (10 ml). Thereafter, a tetrahydrofuran solution (10 ml) containing maleic acid (25 mg) was added to the reaction solution at room temperature. Thereafter, t-butyl methyl ether was added thereto at room temperature, and the obtained mixture was then concentrated under a reduced pressure. Diethyl ether was added to the residue for solidification. This suspension was stirred for 10 minutes while cooling on ice, and a solid was then collected by filtration. The solid was washed with diethyl ether, so as to obtain the subject compound (117 mg).

Workup

  1. additionwas added to the reaction solution at room temperature
  2. concentrationat room temperature, and the obtained mixture was then concentrated under a reduced pressure
  3. additionDiethyl ether was added to the residue for solidification
  4. temperaturewhile cooling on ice
  5. filtrationa solid was then collected by filtration
  6. washThe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-53d0ce7923fb4321bddd80abb534aa47
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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