Methanesulfonic Acid → HCID 86584033, compound

HRID 1862063Notes

Reaction equation

HRID 1862063 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH2:4][CH2:5][C@@H:6]([NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[CH2:7]2.[CH3:34][S:35]([OH:38])(=[O:37])=[O:36]>O1CCCC1>[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH2:4][CH2:5][C@@H:6]([NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[CH2:7]2

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 9846516AR-A000002

Product 1

HCID 86584033HCID 86584033, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide (100 mg, 0.22 mmol) was dissolved in tetrahydrofuran (15 mL) and methanesulfonic acid (42 mg, 0.44 mmol), dissolved in tetrahydrofuran (5 mL), was added dropwise. The solvent was removed in vacuo to give a white solid that was recrystallized from acetone (5 mL) and then from a 15% H2O in acetone solution (7 mL). The crystals were filtered to give 37 mg (31% yield) of light yellow crystals that was stored in an exicator over blue gel: mp 250° C. (decom.). Anal. Calcd. for C27H36N4O2xCH40Sx2H2O: C, 57.9; H, 7.6; N, 9.7. Found: C, 58.1; H, 7.4; N, 9.6.

Workup

  1. additionwas added dropwise
  2. customThe solvent was removed in vacuo
  3. customto give a white solid
  4. customthat was recrystallized from acetone (5 mL)
  5. filtrationThe crystals were filtered
  6. customto give 37 mg (31% yield) of light yellow crystals that

Sources & evidence

ORD record
ord-dd391cbdf86b4fb2a8186db1d5a4ba81
Source dataset
uspto-grants-2003_03
Patent number
US06534652B2

Reaction notes

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