Potassium Carbonate → HCID 51353618, compound

HRID 1879379Notes

Reaction equation

HRID 1879379 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[NH:16][C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C@H:26]2[C:32]3=[N:33][CH:34]=[CH:35][CH:36]=[C:31]3[C@@H:30]([O:37]C(=O)C)[C@H:29]([C:41]3[CH:46]=[C:45]([F:47])[CH:44]=[C:43]([F:48])[CH:42]=3)[CH2:28][CH2:27]2)=[O:24])[CH2:19][CH2:18]1>CO>[O:7]=[C:8]1[NH:16][C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]1[CH:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][C@H:26]2[C:32]3=[N:33][CH:34]=[CH:35][CH:36]=[C:31]3[C@@H:30]([OH:37])[C@H:29]([C:41]3[CH:42]=[C:43]([F:48])[CH:44]=[C:45]([F:47])[CH:46]=3)[CH2:28][CH2:27]2)=[O:24])[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67435744HCID 67435744, compound

Product 1

HCID 51353618HCID 51353618, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

MS(ESI)[M+H+]=578.26. Potassium carbonate (785 mg, 5.68 mmol) was added to the methanol (5 mL) solution of (5S,6S,9R)-5-acetoxy-6-(3,5-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (328 mg, 0.568 mmol) at room temperature. The reaction was stirred at room temperature for 1 h before removal of the solvent. The crude was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed again with water before dried (sodium sulfate), filtered and concentrated. Flash chromatography using methanol in methylene chloride from 0 to 10% gave the desired product (135.3 mg, 42%). HPLC tR=2.17 min, MS(ESI)[M+H+]=536.26, 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.61 (br. s., 1H) 8.52 (d, J=3.78 Hz, 1H) 7.97-8.14 (m, 2H) 7.23-7.58 (m, 2H) 7.02 (dd, J=7.81, 5.29 Hz, 1H) 6.80-6.90 (m, 2H) 6.75 (tt, J=8.84, 2.23 Hz, 1H) 5.94 (br. s., 1H) 5.15 (d, J=9.57 Hz, 1H) 4.31-4.79 (m, 3H) 2.87-3.26 (m, 2H) 2.68-2.80 (m, 1H) 2.03-2.55 (m, 5H) 1.76-2.00 (m, 3H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −108.58 (br. s., 2F).

Workup

  1. customThe crude was partitioned between ethyl acetate and water
  2. customThe ethyl acetate layer was separated
  3. washwashed again with water
  4. dry with materialbefore dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3efc1bc5c6ab4f358b0a3f7f07e6f03d
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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