Potassium Carbonate → HCID 53373729, compound

HRID 909270Notes

Reaction equation

HRID 909270 reaction equation
C([O:4][C@@H:5]([CH3:37])[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]([Br:36])=[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]([Br:36])=[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])[CH3:37])[CH2:9][CH2:10]3)[C:24]=2[CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53373728HCID 53373728, compound

Product 1

HCID 53373729HCID 53373729, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S)-1-[4-(2-{4-amino-2-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-1H-imidazo[4,5-c]pyridin-1-yl}ethyl)piperidin-1-yl]-1-oxopropan-2-yl acetate (300 mg, 0.50 mmol) in MeOH (5 mL) was added K2CO3 (140 mg, 0.01 mmol) and the resulting mixture was stirred for 6 h at room temperature. After the completion of reaction, solids were collected by filtration, washed with water and dried to give the title product. 1H NMR (DMSO-d6) δ; 7.71 (d, J=5.8 Hz, 1H), 7.37 (s, 1H), 6.79 (d, J=5.8 Hz, 1H), 6.67 (s, 1H), 6.39 (s, 2H), 6.07 (s, 2H), 5.30-5.40 (m, 1H), 4.15-4.3 (m, 3H), 3.74 (brd, J=13.2 Hz, 1H), 2.88-3.0 (m, 1H), 2.40-2.55 (m, 1H), 1.62-1.76 (m, 2H), 1.45-1.58 (m, 3H), 1.26 (t, J=8.2 Hz, 3H), 0.87-1.18 (m, 2H); TOF-MS [M+H]+ 550.0915.

Workup

  1. customAfter the completion of reaction, solids
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-14931524579d4552b2eec3d89c0e3047
Source dataset
uspto-grants-2011_09
Patent number
US08017780B1

Reaction notes

Loading…