Ammonium Chloride → HCID 86714736, compound

HRID 2171839Notes

Reaction equation

HRID 2171839 reaction equation
[F:1][C:2]1[C:3]([NH:28][C@@H:29]([C:42]([CH3:45])([CH3:44])[CH3:43])/[CH:30]=[CH:31]/[P:32](=[O:41])([O:37][CH:38]([CH3:40])[CH3:39])[O:33][CH:34]([CH3:36])[CH3:35])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)=[N:6][CH:7]=1.C[O-].[Na+].[NH4+].[Cl-]>CO>[F:1][C:2]1[C:3]([NH:28][C@@H:29]([C:42]([CH3:45])([CH3:44])[CH3:43])/[CH:30]=[CH:31]/[P:32](=[O:41])([O:37][CH:38]([CH3:39])[CH3:40])[O:33][CH:34]([CH3:35])[CH3:36])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 86714734HCID 86714734, compound2×

Product 1

HCID 86714736HCID 86714736, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R,E)-diisopropyl (3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-4,4-dimethylpent-1-en-1-yl)phosphonate, 17a, (1.0 g, 1.51 mmol) in methanol (30 mL) was added sodium methoxide (8.2 mL of 25% wt solution in MeOH). After 3 minutes, the mixture was diluted into aqueous saturated NH4Cl solution and extracted twice with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified via silica gel chromatography (0-15% MeOH/CH2Cl2 gradient) to afford 724 mg of the desired product: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.76 minutes (M+H) 508.13.

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified via silica gel chromatography (0-15% MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-7df93eb805ce4fd1b514f77723f3f9ea
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

Loading…