Lithium Hydroxide → HCID 86729307, compound

HRID 1051547Notes

Reaction equation

HRID 1051547 reaction equation
C([O:4][CH:5]([CH2:17][N:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[CH:29]=[CH:30][C:31]3[N:35]=[CH:34][N:33]([CH3:36])[C:32]=3[CH:37]=2)[CH:23]=1)[C:19](=[O:21])[CH3:20])[CH2:6][N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)(=O)C.[OH-].[Li+]>CCO.O>[CH2:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][N:7]1[CH2:6][CH:5]([OH:4])[CH2:17][N:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[CH:29]=[CH:30][C:31]3[N:35]=[CH:34][N:33]([CH3:36])[C:32]=3[CH:37]=2)[CH:23]=1)[C:19](=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86729308HCID 86729308, compound

Product 1

HCID 86729307HCID 86729307, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(N-(3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenyl)acetamido)propan-2-yl acetate (60 mg, 0.121 mmol) in EtOH (2 ml) and H2O (1 mL) was added lithium hydroxide (10 mg, 0.238 mmol). The mixture was stirred at 25° C. until LCMS indicated completion of the reaction. Solvents were evaporated and the residue dissolved in 30 mL DCM, washed with aq. NaHCO3 and water then dried over anhydrous Na2SO4, and filtrated. Solvent was removed from this filtrate leaving a residue which was then purified by prep-HPLC to afford the desired product as colorless oil (3.7 mg, 6.7%). 1H NMR (400 MHz, METHANOL-d4) δ 8.49 (br. s., 1H), 8.20 (s, 1H), 7.84 (s, 1H), 7.70-7.81 (m, 3H), 7.49-7.67 (m, 2H), 7.33-7.41 (m, 1H), 7.13-7.27 (m, 3H), 7.09 (d, J=6.90 Hz, 1H), 4.31 (br. s., 1H), 4.20 (s, 2H), 4.03 (dd, J=5.21, 13.99 Hz, 1H), 3.96 (s, 3H), 3.73-3.84 (m, 1H), 3.32-3.39 (m, 2H), 2.98-3.19 (m, 4H), 1.97 (s, 3H) LCMS (m/z): 455.2 [M+H]+

Workup

  1. customcompletion of the reaction
  2. customSolvents were evaporated
  3. dissolutionthe residue dissolved in 30 mL DCM
  4. washwashed with aq. NaHCO3 and water
  5. dry with materialthen dried over anhydrous Na2SO4
  6. filtrationfiltrated
  7. customSolvent was removed from this filtrate
  8. customleaving a residue which
  9. customwas then purified by prep-HPLC

Sources & evidence

ORD record
ord-c16f1fa2e50b4fbc83c5ba22bc5890ef
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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