Sodium Hydroxide → HCID 57935726, compound

HRID 1434586Notes

Reaction equation

HRID 1434586 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])=[C:3]1[CH2:35][C:36]([O:38]CC)=[O:37].[OH-].[Na+]>CO.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:23][CH:24]=3)[CH2:15][CH2:14]2)=[O:12])=[C:3]1[CH2:35][C:36]([OH:38])=[O:37]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57935875HCID 57935875, compound

Product 1

HCID 57935726HCID 57935726, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl (1-methyl-3-{[4-(4-{[3-(1-piperidinyl)propyl]oxy}phenyl)-1-piperazinyl]carbonyl}-1H-indol-2-yl)acetate (E60) [54 mg] in methanol [6 ml] and water [0.8 ml] was treated with 2N sodium hydroxide [0.46 ml] and was heated under reflux for 2 h. The reaction mixture was quenched with hydrochloric acid [10 ml] at room temperature. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The organic phase was dried and concentrated in vacuo to give the title compound (20 mg). LCMS RT=2.35 min, 518 (M+H)+

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. customThe reaction mixture was quenched with hydrochloric acid [10 ml] at room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompartitioned between ethyl acetate and water
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b88721f83f6427c96852c8e3eb1d4f0
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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