Methanesulfonic Acid → HCID 178466183, compound

HRID 853022Notes

Reaction equation

HRID 853022 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH:12][C:13]1[S:14]/[C:15](=[CH:19]\[C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[C:23]3[O:30][CH2:31][CH3:32])/[C:16](=[O:18])[N:17]=1)[CH3:2].[CH3:33][S:34]([OH:37])(=[O:36])=[O:35].COC(C)(C)C>C(O)C>[CH3:33][S:34]([OH:37])(=[O:36])=[O:35].[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH:12][C:13]1[S:14]/[C:15](=[CH:19]\[C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[C:23]3[O:30][CH2:31][CH3:32])/[C:16](=[O:18])[N:17]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 15413tert-Butyl methyl etherHCID 178466182HCID 178466182, compound

Product 1

HCID 178466183HCID 178466183, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To the suspension of 2-[2-(2-Ethoxy-phenyl)-ethylamino]-5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one (60 mg, 0.13 mmol) in ethanol (2 mL) was added methanesulfonic acid (9.6 uL, 0.14 mmol) in ethanol (1 mL). After stirring for 30 min, t-butyl methyl ether (5 mL) was added slowly. The mixture was stirred for 3 hours. The solid was collected by filtration and washed with t-butyl methyl ether and dried to give 2-[2-(2-Ethoxy-phenyl)-ethylamino]-5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one; compound with methanesulfonic acid as light yellow solid (66 mg, 91%). LC-MS m/e 448 (MH+).

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with t-butyl methyl ether
  4. customdried

Sources & evidence

ORD record
ord-8651712337364c4082bc8ecd2f236292
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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