Lithium Hydroxide → HCID 44132901, compound

HRID 875962Notes

Reaction equation

HRID 875962 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:29]5[CH:30]=[CH:31][N:32]=[CH:33][C:28]=5[N:27]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])(=O)C.[Li+].[OH-]>C1COCC1.CO.O>[CH:34]1([N:27]2[C:25]3[N:26]=[C:21]([NH:20][C:17]4[N:16]=[CH:15][C:14]([N:11]5[CH2:12][CH2:13][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:9][CH2:10]5)=[CH:19][CH:18]=4)[N:22]=[CH:23][C:24]=3[C:29]3[CH:30]=[CH:31][N:32]=[CH:33][C:28]2=3)[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58299757HCID 58299757, compound

Product 1

HCID 44132901HCID 44132901, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 189 (˜0.5 mmol) in THF/methanol/H2O (3:1:1, 10 mL) was added 12 mg of LiOH and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated and the residue was dissolved in dichloromethane then washed with water and brine then dried. The solvent was evaporated and the residue was purified by chromatography on silica gel eluting with CH2Cl2:methanol:NH4OH (400:10:1) to give compound 188 as a yellow solid (150 mg, 63% in two steps). 1H NMR (500 MHz, DMSO-d6) δ 9.82 (1H, s), 9.27 (1H, s), 9.01 (1H, s), 8.44 (1H, d, J=5 Hz), 8.21 (1H, d, J=10 Hz), 8.07 (1H, d, J=2 Hz), 8.04 (1H, d, J=5 Hz), 7.52 (1H, dd, J=10 Hz, J=2 Hz), 5.37 (1H, p, J=10 Hz), 4.65 (1H, t, J=5 Hz), 4.15 (2H, d, J=5 Hz), 3.65 (2H, m), 3.53 (2H, m), 3.15 (4H, m), 2.40 (2H, m), 2.08 (4H, m), 1.78 (2H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 472.2, Calculated 472.3.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washthen washed with water and brine
  4. customthen dried
  5. customThe solvent was evaporated
  6. customthe residue was purified by chromatography on silica gel eluting with CH2Cl2:methanol:NH4OH (400:10:1)

Sources & evidence

ORD record
ord-4aa9dd0817a84ecca261b4517db3378a
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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