Sodium Methoxide → HCID 68008451, compound

HRID 527044Notes

Reaction equation

HRID 527044 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@@:20]([CH2:25][CH:26]([OH:29])[CH2:27][OH:28])([OH:24])[CH2:19]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.C[O-].[Na+]>CO.[NH4+].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@@:20]([CH2:25][CH:26]([OH:29])[CH2:27][OH:28])([OH:24])[CH2:19]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 68007819HCID 68007819, compound2×

Product 1

HCID 68008451HCID 68008451, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 3-((1R,3S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclohexyl)propane-1,2-diol, 58d, (0.11 g, 0.18 mmol) in MeOH (5 mL) was added sodium methanolate (2 mL of 25% w/v solution, 9.26 mmol) and the reaction mixture was stirred at room temperature. After 20 min, the reaction mixture was diluted with aqueous saturated NH4Cl solution and extracted twice with 20% IPA/CH2Cl2. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification via silica gel chromatography using 5-20% MeOH: CH2Cl2 gradient to afford 56 mg of a white solid.

Workup

  1. extractionextracted twice with 20% IPA/CH2Cl2
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-8cc358e15da942b59885ce45b2e6cf3e
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

Loading…