Sodium Methoxide → HCID 57960829, compound

HRID 449069Notes

Reaction equation

HRID 449069 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:24]3[CH2:27][C@H:26]([CH2:28][O:29]S(C4C=CC(C)=CC=4)(=O)=O)[CH2:25]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:40][O-].[Na+]>CO>[CH3:40][O:29][CH2:28][CH:26]1[CH2:25][CH:24]([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)[N:9]=2)[CH2:27]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178427762HCID 178427762, compound

Product 1

HCID 57960829HCID 57960829, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of cis-toluene-4-sulfonic acid 3-[8-amino-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclobutylmethyl ester (20 mg, 0.04 mmol) in MeOH (2 mL) was added 25% wt. NaOMe in MeOH (25:75, MeONa:MeOH, 13 uL). The resulting mixture was stirred at 50° C. overnight. Reaction was quenched with sat. aq. NaHCO3 solution, extracted with DCM and dried (Na2SO4). The solvent was removed under reduced pressure to give a residue which was then purified by flash chromatography. 1H NMR (400 MHz, CDCl3) δ ppm 2.28-2.43 (m, 2H), 2.54-2.65 (m, 2H), 2.65-2.75 (m, 1H), 3.34 (s, 3H), 3.40-3.46 (m, 2H), 3.59-3.75 (m, 1H), 5.03 (s, 2H), 7.02-7.09 (m, 3H), 7.08-7.18 (m, 4H), 7.33-7.40 (m, 2H), 7.59-7.65 (m, 2H).

Workup

  1. customReaction
  2. customwas quenched with sat. aq. NaHCO3 solution
  3. extractionextracted with DCM
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customto give a residue which
  7. customwas then purified by flash chromatography

Sources & evidence

ORD record
ord-8736cff212b44f80bcf8ee8c92479429
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…