Methanesulfonic Acid → HCID 86663963, compound

HRID 712184Notes

Reaction equation

HRID 712184 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:24](=[O:27])[CH2:25][CH3:26])[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>[CH2:21]([NH:20][C:18]([NH:17][C:15]1[S:16][C:12]2[C:11]([C:24](=[O:27])[CH2:25][CH3:26])=[CH:10][C:9]([OH:8])=[CH:23][C:13]=2[N:14]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 86663964HCID 86663964, compound

Product 1

HCID 86663963HCID 86663963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-(benzyloxy)-7-propionylbenzo[d]thiazol-2-yl)-3-ethylurea (5.50 g, 14.34 mmol) in dichloromethane (50 mL) was added methanesulphonic acid (18.6 mL, 286.8 mmol) at rt. The mixture was stirred for 1 h at rt. After reaction completion (by TLC), was added ice-cold water (100 mL) at 0° C. followed by extraction with EtOAc (3×100 mL). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 100-200 M, 5% MeOH-DCM) to obtain the desired product as an off white solid (4.30 g, 64%). 1H NMR (DMSO-d6): δ 10.95 (br s, 1H), 9.80 (br s, 1H), 7.43 (s, 1H), 7.25 (s, 1H), 6.80 (br s, 1H), 3.15-3.20 (m, 2H), 3.08-3014 (m, 2H), 1.07-1.14 (m, 6H). LCMS: 294.20 [M+H]+.

Workup

  1. customAfter reaction completion (by TLC)
  2. extractionfollowed by extraction with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel 100-200 M, 5% MeOH-DCM)

Sources & evidence

ORD record
ord-0f08dc336bd84607b1b28341d87a6935
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…