Hydrochloric Acid → HCID 118036705, compound

HRID 1778077Notes

Reaction equation

HRID 1778077 reaction equation
[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])=[N:4][C:5]([NH:8][C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:21](OC)[O:22]C)[N:19]=3)[CH2:14][CH2:13][CH2:12]2)=[O:10])=[N:6][CH:7]=1.Cl>O>[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])=[N:4][C:5]([NH:8][C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=[O:22])[N:19]=3)[CH2:14][CH2:13][CH2:12]2)=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118036241HCID 118036241, compound2×

Product 1

HCID 118036705HCID 118036705, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 2E, 25 mg, 0.045 mmol) was treated with HCl (4 M in dioxane, 2 ml, 8.00 mmol) and some drops of water and stirred at room temperature for 2 h. The reaction was quenched by addition of sat. aq. NaHCO3 and extracted with DCM (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was triturated in a hot mixture of EtOAc/heptanes 10:1, the suspension was then centrifuged, the liquid phase was removed, some heptane was added and it was again centrifuged. The liquid phase was removed and the solid was dried under high vacuum to give the title compounds as a colorless powder.

Workup

  1. customThe reaction was quenched by addition of sat. aq. NaHCO3
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was triturated in a hot mixture of EtOAc/heptanes 10:1
  7. customthe liquid phase was removed
  8. additionsome heptane was added
  9. customThe liquid phase was removed
  10. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-c79364fa98084f188f713d078a287336
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…