Sodium Hydroxide → HCID 117952630, compound

HRID 1499278Notes

Reaction equation

HRID 1499278 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:22][CH2:21][C:11]3([CH2:15][NH:14][C@H:13]([C:16]([O:18]CC)=[O:17])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:33]=2)[N:3]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:9][CH2:10][C:11]3([CH2:15][NH:14][C@H:13]([C:16]([OH:18])=[O:17])[CH2:12]3)[CH2:21][CH2:22]2)[CH:5]=[C:4]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([S:38]([CH3:41])(=[O:39])=[O:40])[CH:33]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131734261HCID 131734261, compound

Product 1

HCID 117952630HCID 117952630, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (S)-ethyl 8-(2-amino-6-((5-chloro-3′-(methylsulfonyl)-[1,1′-biphenyl]-2-yl)methoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate (100 mg, 0.13 mmol) in MeOH (3 mL) was added 4 N NaOH (3 mL), and the mixture was stirred at RT for 4 h. The reaction mixture was then concentrated in vacuo. The residue was diluted with water (5 mL) and the pH adjusted to 6-7. The precipitated solid was collected by filtration, the filter cake was washed with cold water, then dried to afford the title compound as an off-white solid isolated as the zwitterionic form.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionThe residue was diluted with water (5 mL)
  3. filtrationThe precipitated solid was collected by filtration
  4. washthe filter cake was washed with cold water
  5. customdried

Sources & evidence

ORD record
ord-a571d8cd6d724c118fc5482d75bfa21c
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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