Methanesulfonic Acid → HCID 57813595, compound

HRID 1941981Notes

Reaction equation

HRID 1941981 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)C1C=CC=CC=1.CS(O)(=O)=O>ClCCl.C(OCC)(=O)C>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([C:11]2[C:12]3[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=3[CH:23]=[C:9]([OH:8])[CH:10]=2)=[N:25][CH:26]=1)#[N:31]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 57813734HCID 57813734, compound

Product 1

HCID 57813595HCID 57813595, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 1-[5-Benzyloxy-7-(5-cyano-pyridin-2-yl)-benzothiazol-2-yl]-3-ethyl-urea (110 mg, 0.26 mmol) in anhydrous dichloromethane (3 ml) was treated with methanesulfonic acid (1 ml) and kept at ambient temperature for 2 h. The organic layer was diluted with ethyl acetate then washed with water (3×30 ml), dried (MgSO4) and the solvent removed in vacuo to give the crude 1-[7-(5-Cyano-pyridin-2-yl)-5-hydroxy-benzothiazol-2-yl]-3-ethyl-urea (80 mg, 90%) as an off-white solid which was used without further purification.

Workup

  1. washthen washed with water (3×30 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-55d5aedf26c446df9b62f37912eeb9e7
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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