Potassium Carbonate → HCID 178516527, compound

HRID 473901Notes

Reaction equation

HRID 473901 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][N:9]2[C:15]([N:17]2[CH2:23][C:22]3[CH:24]=[C:25]([C:28]4[CH:29]=[C:30]5[N:36](C(OCC(C)C)=O)[CH:35]=[N:34][C:31]5=[N:32][CH:33]=4)[CH:26]=[CH:27][C:21]=3[O:20][CH2:19][CH2:18]2)=[O:16])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C.C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][N:9]2[C:15]([N:17]2[CH2:23][C:22]3[CH:24]=[C:25]([C:28]4[CH:29]=[C:30]5[N:36]=[CH:35][NH:34][C:31]5=[N:32][CH:33]=4)[CH:26]=[CH:27][C:21]=3[O:20][CH2:19][CH2:18]2)=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 708152472-methylpropyl 6-(4-{[2-(3-fluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate

Product 1

HCID 178516527HCID 178516527, compoundYield 289.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-methylpropyl 6-(4-{[2-(3-fluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate (0.19 g, 0.32 mmol) and potassium carbonate (0.20 g, 1.4 mmol) in methanol (10 mL) was stirred for 45 minutes at 25° C. The mixture was diluted with ethyl acetate (80 mL) washed with water (50 mL) and brine (25 mL), then dried over anhydrous sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel (methanol/ethyl acetate 1:10). Residue obtained by the concentration of product containing fractions was stirred 18 hours at 25° C. in diethyl ether (20 mL) and the solid product thus formed was isolated by filtration to give 2-(3-fluorophenyl)-1-{[7-(3H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]carbonyl}piperidin-4-one (0.45 g, 27% yield). 1H NMR (400 MHz, d6-DMSO): 8.62 (s, 1H), 8.47 (s, 1H), 8.18 (s, 1H), 7.69 (d, 1H), 7.57 (d, 1H), 7.24 (q, 1H), 7.10-7.01 (m, 4H), 5.19 (t, 1H), 4.61 (m, 2H), 4.24 (m, 2H), 3.72 (m, 3H), 3.41 (m, 2H), 2.84 (m, 2H), 2.61 (m, 1H), 2.34 (d, 1H); MS (EI) for C27H24FN5O3: 486 (MH+).

Workup

  1. washwashed with water (50 mL) and brine (25 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (methanol/ethyl acetate 1:10)
  6. customResidue obtained by the concentration of product
  7. additioncontaining fractions
  8. customthe solid product thus formed
  9. customwas isolated by filtration

Sources & evidence

ORD record
ord-7bcbc20c0b3d4864b976d8fdb95bae52
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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