Potassium Carbonate → HCID 86625992, compound

HRID 1992341Notes

Reaction equation

HRID 1992341 reaction equation
Cl[CH2:2][CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].[C:17]([O:21][C:22]([N:24]1[CH2:31][CH:30]2[O:32][CH:26]([CH2:27][NH:28][CH2:29]2)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:5]=[C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)[CH2:3][CH2:2][N:28]1[CH2:27][CH:26]2[O:32][CH:30]([CH2:31][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH2:25]2)[CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 68521888HCID 68521888, compound

Product 1

HCID 86625992HCID 86625992, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

1-(3-Chloropropionyl)-2,3-dihydro-1H-indole-5-carbonitrile (3.07 g, 0.031 mol; see step (v) above), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (3 g, 0.031 mol; see WO 01/28992) and potassium carbonate (6.43 g, 0.0465 mol) were taken in dry acetonitrile (30 mL) and stirred at 60° C. overnight under a nitrogen atmosphere. The reaction mixture was filtered and concentrated under reduced pressure to provide a crude product. This product was then purified by column chromatography using methanol in DCM as eluent to yield the sub-title compound as pale yellow solid. Yield: 5 g.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customto provide a crude product
  4. customThis product was then purified by column chromatography

Sources & evidence

ORD record
ord-65be18fa3d8140c38925fe3def121aa7
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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