Hydrochloric Acid → HCID 67130014, compound

HRID 1038828Notes

Reaction equation

HRID 1038828 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]3[O:31][CH:30]=[CH:29][C:7]=3[N:8]=[C:9]([NH:11][C:12]3[CH:20]=[C:19]4[C:15]([C:16](C)=[N:17][N:18]4C4CCCCO4)=[C:14](F)[CH:13]=3)[N:10]=2)[CH2:3][CH2:2]1.Cl.O1CCOC[CH2:34]1>>[CH:1]1([NH:4][C:5]2[C:6]3[O:31][CH:30]=[CH:29][C:7]=3[N:8]=[C:9]([NH:11][C:12]3[CH:20]=[C:19]4[C:15]([CH:16]=[N:17][NH:18]4)=[C:14]([CH3:34])[CH:13]=3)[N:10]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86665107HCID 86665107, compound

Product 1

HCID 67130014HCID 67130014, compoundYield 20%

Conditions

Temperature
50 °C

Procedure

A flask was charged with N4-cyclopropyl-N2-(4-fluoro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)furo[3,2-d]pyrimidine-2,4-diamine (0.19 g, 0.45 mmol, prepared using B from Preparation #A.1 with Preparation #AN.1) and 4 M HCl in 1,4-dioxane (2 mL). The mixture was stirred at about 50° C. for about 2 h, cooled to rt, concentrated under reduced pressure and purified by reverse phase HPLC (Table 2, Method o) to give N4-cyclopropyl-N2-(4-methyl-1H-indazol-6-yl)furo[3,2-d]pyrimidine-2,4-diamine (0.030, 20%): LC/MS (Table 2, Method h) Rt=1.85 min; MS m/z: 321 (M+H)+. Syk IC50=A

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated under reduced pressure
  3. custompurified by reverse phase HPLC (Table 2, Method o)

Sources & evidence

ORD record
ord-d486badac6d6486a964ae4581913a371
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

Loading…