Methanesulfonic Acid → HCID 178467899, compound

HRID 2065811Notes

Reaction equation

HRID 2065811 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([CH2:17][OH:18])[CH2:16][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][O:31][CH2:32][CH3:33])=[N:27][C:22]2=[CH:21][CH:20]=1.[CH3:35][S:36](O)(=[O:38])=[O:37]>ClCCl.CO.CO>[CH3:35][S:36]([O:18][CH2:17][C:14]1([C:12]2[NH:13][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[C:10]([C:19]3[N:24]=[C:23]4[O:25][C:26]([NH:28][C@@H:29]([CH3:34])[CH2:30][O:31][CH2:32][CH3:33])=[N:27][C:22]4=[CH:21][CH:20]=3)[N:11]=2)[CH2:15][CH2:16]1)(=[O:38])=[O:37]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178467897HCID 178467897, compound

Product 1

HCID 178467899HCID 178467899, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

[1-[5-(2,4-Difluorophenyl)-4-[2-[[(1S)-2-ethoxy-1-methyl-ethyl]amino]oxazolo[5,4-b]pyridin-5-yl]-1H-imidazol-2-yl]cyclopropyl]methanol (0.56 g, 1.19 mmol) is dissolved in a 1:1 mixture of dichloromethane/methanol (12 mL total). A 0.5 M solution of methanesulfonic acid in methanol (2.37 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 (0.64 g, 96%). LC-ES/MS m/z 470.1 (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-014ec4c92b094ed0bf8d57802148625a
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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