Hydrochloric Acid → HCID 68172807, compound

HRID 2404211Notes

Reaction equation

HRID 2404211 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH:15]3[CH2:20][CH2:19][CH:18]([C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16]3)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[CH2:25]([O:27][C:28](=[O:32])[CH2:29][CH2:30][NH2:31])[CH3:26].Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:25]([O:27][C:28](=[O:32])[CH2:29][CH2:30][NH:31][CH2:2][C:3](=[O:4])[N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH:15]3[CH2:20][CH2:19][CH:18]([C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16]3)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)[CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 419889Ethyl 3-aminopropanoateHCID 68172805HCID 68172805, compound

Product 1

HCID 68172807HCID 68172807, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of crude 2-chloro-1-[5-(4-trifluoromethyl-cyclohexyloxy)-2,3-dihydro-indol-1-yl]-ethanone (80 mg, 0.22 mmol), 3-amino-propionic acid ethyl ester as HCl salt (68 mg, 0.44 mmol) and potassium carbonate (98 mg, 0.71 mmol) in acetonitrile (2 mL) was heated to reflux for 4 hrs. The mixture was treated with water and extracted with ether. The organic phase was dried over MgSO4, concentrated, and purified via a silica gel column to give desired product (11 mg, yield 10%). ESI-MS: 443.20 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hrs
  3. extractionextracted with ether
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. custompurified via a silica gel column

Sources & evidence

ORD record
ord-d68867f155724d0cbcf13caf83f11f10
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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