Water → HCID 59323250, compound

HRID 2390086Notes

Reaction equation

HRID 2390086 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][N:8]2[CH2:17][CH2:18][CH2:19][NH2:20])=[CH:4][CH:3]=1.C(=O)(OC1C=CC=CC=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([N:38]([CH3:40])[CH3:39])[CH:33]=1)N.C([N:44]([CH2:47]C)CC)C.[OH2:49]>C1(C)C=CC=CC=1>[CH3:40][N:38]([CH3:39])[C:34]1[CH:33]=[C:32]([NH:44][C:47]([NH:20][CH2:19][CH2:18][CH2:17][N:8]2[CH:7]([CH2:6][C:5]3[CH:21]=[CH:22][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)=[O:49])[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 593233653-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]propanamineHCID 68522450HCID 68522450, compound

Product 1

HCID 59323250HCID 59323250, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 mg of 3-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]propanamine obtained in Example 214-b), 28 mg of (3-dimethylaminophenyl)phenyl carbamate, and 31 mg of triethylamine were dissolved in 1 mL of toluene, followed by stirring under reflux for 30 minutes. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (chloroform:methanol=10:1) to obtain 22.3 mg (yield 48%) of a title compound as a pale yellow oily substance.

Workup

  1. temperatureunder reflux for 30 minutes
  2. additionwas added to the reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was then washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified

Sources & evidence

ORD record
ord-0ff6ae20227d476d9a482b1efc41c2ea
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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