Acetonitrile → HCID 131733252, compound

HRID 509914Notes

Reaction equation

HRID 509914 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([NH:12]C(OC(C)(C)C)=O)[CH2:7]1)[CH3:2].[Br:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.C(#N)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>>[F:36][C:37]([F:42])([F:41])[C:38]([O-:40])=[O:39].[Br-:21].[NH2:12][CH:8]1[CH2:9][CH2:10][CH2:11][N+:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[CH2:7]1.[NH2:12][CH:8]1[CH2:9][CH2:10][CH2:11][N+:6]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH2:7]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 127769961-(3-Bromopropyl)-4-methoxybenzeneHCID 84002672HCID 84002672, compound2×

Product 1

HCID 131733252HCID 131733252, compound

Procedure

To a solution of (3-tert-butoxycarbonylamino-piperidin-1-yl)-acetic acid ethyl ester (Intermediate 3.1.1, 800 mg, 2.3 mmol) and 1-(3-bromo-propyl)-4-methoxy-benzene (614 mg, 2.6 mmol) in acetonitrile (20 mL) K2CO3 (154 mg, 1.1 mmol) is added and the mixture heated at reflux with stirring for 72 hours. After removal of insolubles by filtration and evaporation of the solvent at reduced pressure the resulting material is dissolved in dry dichloromethane (6 mL) and trifluoroacetic acid (1 mL, 13 mmol) is added. After stirring of the resulting solution at room temperature for 4 hours volatiles are evaporated under reduced pressure and the resulting solid is co-evaporated several times with toluene. The material thus obtained is used as such in the next step. Yield: 0.58 g.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. customAfter removal of insolubles
  4. filtrationby filtration and evaporation of the solvent at reduced pressure the resulting material
  5. dissolutionis dissolved in dry dichloromethane (6 mL)
  6. stirringAfter stirring of the resulting solution at room temperature for 4 hours volatiles
  7. customare evaporated under reduced pressure
  8. customThe material thus obtained

Sources & evidence

ORD record
ord-721a162234704bb2b77a516a8f812ca5
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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