HCID 18925017, compound → HCID 18925064, compound

HRID 1288886Notes

Reaction equation

HRID 1288886 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:17]([O:20]C=C)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].[ClH:28].CO>>[ClH:28].[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:17]([OH:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

3

Reactant 2

HCID 18925017HCID 18925017, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 18925064HCID 18925064, compound

Procedure

(3-Ethynyl-phenyl)-[7-(2-methoxy-ethoxy)-6-vinyloxy-quinazolin-4-yl]-amine (20 mg; from Example 48) was hydrolyzed by treatment with 6M HCl/methanol (30:70; 3 mL) at 50° C. for 5 days. The solution was concentrated in vacuo, and the residue was partitioned between CHCl3 and brine at a pH of about 7. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the title product as its free base (15 mg), which was converted to its HCl salt according to the procedure described for Example 28 (M.P. 135°-150° C. (dec); LC-MS: 336 (MH+); anal. RP-HPLC RT: 3.77 min).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between CHCl3 and brine at a pH of about 7
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-457f37bb2b5443469c994612dc2d166f
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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