Potassium Carbonate → HCID 53389676, compound

HRID 909272Notes

Reaction equation

HRID 909272 reaction equation
C([O:4][C@@H:5]([CH3:39])[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[C:24]3[CH:23]=[CH:22][N:21]=[C:20]([NH2:25])[C:19]=3[N:18]=[C:17]2[S:26][C:27]2[C:35]([N:36]([CH3:38])[CH3:37])=[CH:34][C:30]3[O:31][CH2:32][O:33][C:29]=3[CH:28]=2)[CH2:10][CH2:9]1)=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:25][C:20]1[C:19]2[N:18]=[C:17]([S:26][C:27]3[C:35]([N:36]([CH3:38])[CH3:37])=[CH:34][C:30]4[O:31][CH2:32][O:33][C:29]=4[CH:28]=3)[N:16]([CH2:15][CH2:14][CH:11]3[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C@@H:5]([OH:4])[CH3:39])[CH2:9][CH2:10]3)[C:24]=2[CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53389656HCID 53389656, compound

Product 1

HCID 53389676HCID 53389676, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S)-1-[4-(2-{4-amino-2-[(6-(dimethylamino)-1,3-benzodioxol-5-yl)sulfanyl]-1H-imidazo[4,5-c]pyridin-1-yl}ethyl)piperidin-1-yl]-1-oxopropan-2-yl acetate (171 mg, 0.32 mmol) in MeOH (3.0 mL) was added K2CO3 (89 mg, 0.64 mmol) and resulting mixture was stirred for 6 h room temperature. After completion of the reaction, the solvent was evaporated under reduced pressure and residue was purified by flash column chromatography. The product was eluted with 10% MeOH in dichloromethane. 1H NMR (DMSO-d6) δ 7.1 (d, J=5.8 Hz, 1H), 7.0 (s, 1H), 6.78 (d, J=5.8 Hz, 1H), 6.41 (s, 2H), 6.18 (s, 1H), 5.94 (s, 2H), 7.78 (d, J=7.4 Hz, 1H), 4.37 (qin, J=5.0 Hz, 1H), 4.27 (t, J=11.3 Hz, 1H), 4.09-4.2 (m, 2H), 3.16 (d, J=5.0 Hz, 1H), 2.77-2.9 (m, 1H), 2.63 (s, 6H), 2.38-2.5 (m, 1H), 1.66 (d, J=11.7 Hz, 2H), 1.53 (q, J=6.6 Hz, 2H), 1.35-1.5 (m, 1H), 1.13 (t, J=5.0 Hz, 3H), 0.85-1.1 (m, 2H); TOF-MS [M+H]+ 513.22.

Workup

  1. customresulting mixture
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated under reduced pressure and residue
  4. customwas purified by flash column chromatography
  5. washThe product was eluted with 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-00b334133e8347b3839a3fd145546f53
Source dataset
uspto-grants-2011_09
Patent number
US08017780B1

Reaction notes

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