HCID 11703778, compound → HCID 66924130, compound

HRID 1364411Notes

Reaction equation

HRID 1364411 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:23][O:24]COC)[CH2:9][O:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[C:13]([NH2:22])=[N:14][C:15]([NH2:21])=[N:16]3)=[CH:4][CH:3]=1>CO.Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:9][O:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[C:13]([NH2:22])=[N:14][C:15]([NH2:21])=[N:16]3)[CH2:23][OH:24])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 11703778HCID 11703778, compound

Product 1

HCID 66924130HCID 66924130, compoundYield 123.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

5-[2-(4-Chlorophenyl)-3-methoxymethoxy-propoxy]-quinazoline-2,4-diamine (Step 6, Example 68) (68 mg; 0.17 mmol) is dissolved in methanol (2 mL), and diluted with 4M HCl in dioxane (1 mL). The reaction is heated in a sealed tube to 60° C. overnight. The solvent is removed under N2 flow. The resulting solid is triturated with 20% MeOH/Ether, and the resulting title compound is filtered and dried under vacuum at 35° C. for 3 hours providing a total of 40 milligrams of 2-(4-chlorophenyl)-3-(2,4-diaminoquinazolin-5-yloxy)-propan-1-ol hydrochloride.

Workup

  1. customThe solvent is removed under N2 flow
  2. customThe resulting solid is triturated with 20% MeOH/Ether
  3. filtrationthe resulting title compound is filtered
  4. customdried under vacuum at 35° C. for 3 hours

Sources & evidence

ORD record
ord-69bedf8339fc420bb1bada253e776b3a
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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