Sodium Chlorite → HCID 178480355, compound

HRID 428568Notes

Reaction equation

HRID 428568 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 2

HCID 23668197Sodium ChloriteHCID 178480353HCID 178480353, compound

Product 1

HCID 178480355HCID 178480355, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

To 750 mg (1.6 mmol) of 8-[4-[(Cis)-4-(5-cyano-1-methyl-1H-indole-3-yl)cyclohexyl]-1-piperazinyl]-6-quinolinecarbaldehyde in 60 mL of t-BuOH and 8 mL of CH3CHC(CH3)2 at 23° C. was added a solution of 1.3 mg (14.4 mmol) NaClO2, 1.3 g (10.8 mmol) NaH2PO4 in 3 ml water. After stirring at 23° C. for 12 hours, the volatiles were removed by rotary evaporation. The reaction mixture was transferred to a separatory funnel and partitioned between water and CH2Cl2. The organics were washed with brine, dried over MsSO4, and chromatographed on silica gel eluting with 20:1 CH2Cl2:MeOH containing 5% glacial HOAc. The product fractions were pooled, stripped, and treated with 75 mg (0.83 mmol) of (CO2H)2 in absolute EtOH to give 390 mg (0.6 mmol, a 38% yield) of the oxalate salt of the title compound as a tan crystalline solid. mp: 230° C.; MS (ES) m/z: 494 (MH)+.

Workup

  1. customthe volatiles were removed by rotary evaporation
  2. customThe reaction mixture was transferred to a separatory funnel
  3. custompartitioned between water and CH2Cl2
  4. washThe organics were washed with brine
  5. customdried over MsSO4
  6. customchromatographed on silica gel eluting with 20:1 CH2Cl2
  7. customto give 390 mg (0.6 mmol

Sources & evidence

ORD record
ord-e0ab9415319e447eaa40458105aa075a
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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