Methanesulfonic Acid → HCID 178495113, compound

HRID 2065807Notes

Reaction equation

HRID 2065807 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])=[C:7]([C:9]3[N:14]=[C:13]4[O:15][C:16]([NH:18][C@@H:19]([CH3:24])[CH2:20][CH2:21][O:22][CH3:23])=[N:17][C:12]4=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1.[CH3:33][S:34]([OH:37])(=[O:36])=[O:35]>ClCCl.CO>[CH3:33][S:34]([OH:37])(=[O:36])=[O:35].[CH:1]1([C:4]2[NH:5][C:6]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])=[C:7]([C:9]3[N:14]=[C:13]4[O:15][C:16]([NH:18][C@@H:19]([CH3:24])[CH2:20][CH2:21][O:22][CH3:23])=[N:17][C:12]4=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178495112HCID 178495112, compound

Product 1

HCID 178495113HCID 178495113, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

5-[2-Cyclopropyl-5-(2,4-difluorophenyl)-1H-imidazol-4-yl]-N-[(1S)-3-methoxy-1-methyl-propyl]oxazolo[5,4-b]pyridin-2-amine (0.090 g, 0.23 mmol) is dissolved in a 1:1 mixture of dichloromethane and methanol (3 mL total). A 0.5 M solution of methanesulfonic acid in methanol (0.47 mL) is added dropwise to the solution. The mixture is stirred at RT for 30 min and then the solvent is evaporated under reduced pressure. The residue is mixed with methanol and concentrated twice to afford the title compound (0.111 g, 89%). LC-ES/MS m/z 440 (M+1).

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. additionThe residue is mixed with methanol
  3. concentrationconcentrated twice

Sources & evidence

ORD record
ord-102839424e0f49b7b09255eee761827a
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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