Water → HCID 178480356, compound

HRID 428569Notes

Reaction equation

HRID 428569 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C@H:13]1[CH2:18][CH2:17][C@H:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[C:27]([CH:35]=[O:36])[CH:28]=[C:29]4[C:34]=3[N:33]=[CH:32][CH:31]=[CH:30]4)[CH2:21][CH2:20]2)[CH2:15][CH2:14]1)#[N:2].[O-:37]Cl=O.[Na+].CC(O)(C)C.O>CCO>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C@H:13]1[CH2:18][CH2:17][C@H:16]([N:19]2[CH2:20][CH2:21][N:22]([C:25]3[CH:26]=[C:27]([C:35]([OH:37])=[O:36])[CH:28]=[C:29]4[C:34]=3[N:33]=[CH:32][CH:31]=[CH:30]4)[CH2:23][CH2:24]2)[CH2:15][CH2:14]1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 23668197Sodium ChloriteHCID 178480354HCID 178480354, compound

Product 1

HCID 178480356HCID 178480356, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The trans was obtained by the process described for Example 73 by combining 0.30 g (.60 mmol) 8-[4-[(Trans)-4-(5-cyano-1-methyl-1H-indole-3-yl)cyclohexyl]-1-piperazinyl]-6-quinolinecarbaldehyde, 0.48 g (5.5 mmol) NaClO2, 0.48 g (4.1mmol) NaH2PO4, 24 mL t-BuOH, 3 mLCH3CHC(CH3)2, and 6 ml water. The product fractions were pooled, striped, and treated with 54 mg (0.60 mmol) of (CO2H)2 in absolute EtOH to give 97 mg (.16 mmol, a 10% yield) mp: 275° C. MS (ES) m/z: 494 (MH)+.

Workup

  1. customThe trans was obtained by the process
  2. customto give 97 mg (.16 mmol

Sources & evidence

ORD record
ord-b81da6b73aa8498b96d06aa33f39542b
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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