Lithium Hydroxide → HCID 69522621, compound

HRID 1181503Notes

Reaction equation

HRID 1181503 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C:12]([NH:14][CH2:15][CH:16]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[C:17]([O:19]CC)=[O:18])=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH-].[Li+]>C1COCC1>[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C:12]([NH:14][CH2:15][CH:16]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=3)[C:17]([OH:19])=[O:18])=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69522010HCID 69522010, compound

Product 1

HCID 69522621HCID 69522621, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-{[(isoquinolin-5-ylamino)carbonyl]amino}-2-[4-(trifluoromethyl)benzyl]propanoate (Example 129, 23 mg, 0.05 mmol) in aqueous THF (1:1, 2 ml) was treated with lithium hydroxide (5 mg, 0.1 mmol) and stirred at room temperature for 20 h. The mixture was evaporated then partitioned between 7% aqueous citric acid and dichloromethane (2:1, 6 ml). A precipitate formed which was collected by filtration and dried azeotropically by adding toluene and evaporating to give the desired compound (8.4 mg). m/z (ES+) 418 (M+H)+.

Workup

  1. customThe mixture was evaporated
  2. customthen partitioned between 7% aqueous citric acid and dichloromethane (2:1, 6 ml)
  3. customA precipitate formed which
  4. filtrationwas collected by filtration
  5. customdried azeotropically
  6. additionby adding toluene
  7. customevaporating

Sources & evidence

ORD record
ord-c180cc0b9b5843b08f7e6adcc2f86bc5
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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