1-Phenethylamine → HCID 86595630, compound

HRID 1833126Notes

Reaction equation

HRID 1833126 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]([NH:11][C:12]([CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:38]=[CH:39][CH:40]=1)[C:19]([C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[C:24]([C:35]([OH:37])=[O:36])=[CH:23][N:22]=1)=[O:20])=[O:13])([CH3:10])[CH3:9].[CH3:41][CH:42](N)[C:43]1C=CC=[CH:45][CH:44]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:34][O:33][C:27]1[CH:26]=[C:25]2[C:30](=[CH:29][C:28]=1[O:31][CH3:32])[C:21]([C:19](=[O:20])[C:18]1[CH:38]=[CH:39][CH:40]=[C:16]([O:15][CH2:14][C:12](=[O:13])[NH:11][CH:8]([C:10]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH3:9])[CH:17]=1)=[N:22][CH:23]=[C:24]2[C:35]([OH:37])=[O:36]

Participants

4

Reactant 2

HCID 74081-PhenethylamineHCID 86595631HCID 86595631, compound

Product 1

HCID 86595630HCID 86595630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The resin bound activated ester (intermediate in the preparation of 1-[3-(Isopropylcarbamoyl-methoxy)-benzoyl]-6,7-dimethoxy-isoquinoline-4-carboxylic acid; compound with trifluoro-acetic acid (Example 37)) (225 mg, 0.19 mmol) was combined with 3 ml of methylene chloride and 0.05 ml of α-methylbenzyl amine (0.4 mmol). The mixture was shaken for 15 minutes under argon at room temperature. The mixture was filtered and the filter cake was washed with methylene chloride. The filtrate was evaporated to dryness. The residue was saponified by dissolving in 1 ml of methanol containing 0.5 ml of 1N sodium hydroxide solution and several drops of tetrahydrofuran. The mixture was stirred at room temperature for 4 hrs and then evaporated to dryness. The residue was purified through a reverse phase preparative HPLC to give 6,7-Dimethoxy-1-{3-[(1-phenyl-ethylcarbamoyl)-methoxy]-benzoyl}-isoquinoline-4-carboxylic acid; compound with trifluoro-acetic acid, as a fluffy solid (30 mg).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with methylene chloride
  3. customThe filtrate was evaporated to dryness
  4. dissolutionby dissolving in 1 ml of methanol containing 0.5 ml of 1N sodium hydroxide solution and several drops of tetrahydrofuran
  5. stirringThe mixture was stirred at room temperature for 4 hrs
  6. customevaporated to dryness
  7. customThe residue was purified through a reverse phase preparative HPLC

Sources & evidence

ORD record
ord-90464c08bb604999a97d552e28228d52
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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