HCID 18925017, compound → HCID 18925064, compound

HRID 1869095Notes

Reaction equation

HRID 1869095 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-50ef2846854644cca7fea8fc304cb374
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

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