Lithium Hydroxide → HCID 86729307, compound

HRID 1399921Notes

Reaction equation

HRID 1399921 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-1e4f088a0d2b4704831120d4c8b5ecd7
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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