Hydrochloric Acid → HCID 59323077, compound

HRID 2390066Notes

Reaction equation

HRID 2390066 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][NH:14][CH2:15][C:16]1[CH:27]=[CH:26][C:19]([NH:20]C(OCC)=O)=[CH:18][CH:17]=1)[CH:6]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[CH2:5]2.[OH-:36].[Li+].Cl.[CH2:39]1[CH2:43][O:42]CC1>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][NH:14][CH2:15][C:16]1[CH:27]=[CH:26][C:19]([NH:20][CH2:39][C:43]([OH:36])=[O:42])=[CH:18][CH:17]=1)[CH:6]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1)[CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68519006HCID 68519006, compound

Product 1

HCID 59323077HCID 59323077, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]-N-ethoxycarbonylaniline (10 mg, 0.02 mmol) obtained in Example 142 and lithium hydroxide.monohydrate (41 mg, 1.0 mmol) were dissolved in 1 mL of THF and 0.5 mL of water, followed by stirring at room temperature overnight. After completion of the reaction, 2N hydrochloric acid was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 3 mg (yield 44.2%) of a title compound as a pale yellow oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was then washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5445c422d9c4d59ad31f900ef81daff
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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