Methanesulfonic Acid → HCID 178495115, compound

HRID 2065809Notes

Reaction equation

HRID 2065809 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][C:12]([C:14]2([CH3:18])[CH2:17][O:16][CH2:15]2)=[N:11][C:10]=1[C:19]1[N:24]=[C:23]2[O:25][C:26]([NH:28][C@@H:29]([CH3:34])[CH2:30][CH2:31][O:32][CH3:33])=[N:27][C:22]2=[CH:21][CH:20]=1.[CH3:35][S:36]([OH:39])(=[O:38])=[O:37]>ClCCl.CO.CO>[CH3:35][S:36]([OH:39])(=[O:38])=[O:37].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][C:12]([C:14]2([CH3:18])[CH2:17][O:16][CH2:15]2)=[N:11][C:10]=1[C:19]1[N:24]=[C:23]2[O:25][C:26]([NH:28][C@@H:29]([CH3:34])[CH2:30][CH2:31][O:32][CH3:33])=[N:27][C:22]2=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178495114HCID 178495114, compound

Product 1

HCID 178495115HCID 178495115, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

5-[5-(2,4-Difluorophenyl)-2-(3-methyloxetan-3-yl)-1H-imidazol-4-yl]-N-[(1S)-3-methoxy-1-methyl-propyl]oxazolo[5,4-b]pyridin-2-amine (0.72 g, 1.54 mmol) is dissolved in a 1:1 mixture of dichloromethane/methanol (15 mL total). A 0.5 M solution of methanesulfonic acid in methanol (3.07 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 triturated with tert-butyl methyl ether to afford the title compound as a brown solid (0.841 g, 97%). LC-ES/MS m/z 470 (M+1).

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. customThe residue is triturated with tert-butyl methyl ether

Sources & evidence

ORD record
ord-6837a058e1d34bc9ab63816e7493c300
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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