Sodium Hydroxide → HCID 118093883, compound

HRID 1056966Notes

Reaction equation

HRID 1056966 reaction equation
[OH-].[Na+].[CH:3]1([CH2:7][O:8][C:9]2[C:17]3[N:16]([CH2:18][CH2:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:15](=[O:26])[N:14]([CH3:27])[C:13]=3[CH:12]=[CH:11][C:10]=2[C:28]2[C:29]3[CH:38]=[CH:37][N:36](S(C4C=CC(C)=CC=4)(=O)=O)[C:30]=3[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=2)[CH2:6][CH2:5][CH2:4]1>O.CO>[CH:3]1([CH2:7][O:8][C:9]2[C:17]3[N:16]([CH2:18][CH2:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:15](=[O:26])[N:14]([CH3:27])[C:13]=3[CH:12]=[CH:11][C:10]=2[C:28]2[C:29]3[CH:38]=[CH:37][NH:36][C:30]=3[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118093765HCID 118093765, compound

Product 1

HCID 118093883HCID 118093883, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A 3.0 M solution of sodium hydroxide in water (0.40 L) was added to the solution of 4-(cyclobutylmethoxy)-1-methyl-5-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl}-3-(2-piperidin-4-ylethyl)-1,3-dihydro-2H-benzimidazol-2-one (20.0 mg, 0.031 mmol) in methanol (1.0 mL), and the resultant reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (1.1 mg, 7%). LCMS calculated for C28H36N5O3 (M+H)+: m/z=490.3. found: 490.3.

Workup

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was purified via preparative LCMS (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-2f3cea05f1ac46faa06be6ddbd7ed3aa
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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