Hydrochloric Acid → HCID 66879075, compound

HRID 2265878Notes

Reaction equation

HRID 2265878 reaction equation
Cl.NO.[OH-].[Na+].[F:6][C:7]1[CH:47]=[CH:46][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH2:32][CH2:33][CH2:34][N:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)[CH:27]=4)[CH:22]3[C:42]([O:44]C)=[O:43])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1.Cl>O.O1CCOCC1>[F:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH2:32][CH2:33][CH2:34][N:35]5[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]5)[CH:27]=4)[CH:22]3[C:42]([OH:44])=[O:43])(=[O:19])=[O:20])=[CH:14][CH:13]=2)=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 443297Hydroxyamine hydrochloride2×HCID 68679430HCID 68679430, compound

Product 1

HCID 66879075HCID 66879075, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 61 mg (0.88 mmol) of hydroxylamine hydrochloride in 1 ml of H2O is mixed with a solution of 56 mg (1.4 mmol) of NaOH in 0.5 ml of H2O and stirred for 10 minutes. At 0° C., a solution of 240 mg (0.4 mmol) of methyl 2-[4-(4-fluorophenoxy)-benzenesulfonyl]-6-[3-(4-methylpiperazin-1-yl)propoxy]-1,2,3,4-tetrahydroisoquinoline-1-carboxylate in 0.5 ml of dioxane is added, and the mixture is stirred at 0° C. To achieve complete conversion, 61 mg (0.88 mmol) of hydroxylamine hydrochloride and 56 mg (1.4 mmol) of NaOH are added twice more. For work up, the mixture is neutralized with 1 N HCl and extracted with ethyl acetate. The organic phase is separated off, dried with MgSO4 and concentrated. Chromatography of the residue on silica gel affords the hydroxamic acid (exemplary compound 3) as colorless solid in 46% yield, and the carboxylic acid (exemplary compound 4), likewise as colorless solid in a yield of 15%.

Workup

  1. stirringthe mixture is stirred at 0° C
  2. additionare added twice more
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is separated off
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-672faaf6f7074755ade2c14446e73763
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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