Hydrochloric Acid → HCID 53630903, compound

HRID 2102458Notes

Reaction equation

HRID 2102458 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH:23]4[CH2:28][O:27][CH2:26][CH2:25][N:24]4[C:29]([O-])=O)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.C(OCC)C>CO.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][CH:28]4[O:27][CH2:26][CH2:25][NH:24][CH2:29]4)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 131727582HCID 131727582, compound

Product 1

HCID 53630903HCID 53630903, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1,1-dimethylethyl 2-({[4-[(3,4-dichlorophenyl)amino]-6-(methoxy)quinazolin-7-yl]oxy}morpholine-4-carboxylate (4.77 g, 8.91 mmol) in methanol (50 mL) was added a 4M solution of HCl in 1,4-dioxane (50 mL), and the reaction mixture was refluxed for 5 min. After cooling to room temperature, diethyl ether (100 mL) was added and the precipitate was filtered and dried. The solid was dissolved in methanol (200 mL) and treated with Bio-Rad 1-X8 resin hydroxide form until pH 8. Filtration and concentration in vacuo provided 3.32 g (86%) of N-(3,4-dichlorophenyl)-6-(methyloxy)-7-[(morpholin-2-ylmethyl)oxy]quinazolin-4-amine as a brown solid. 1H NMR (400 MHz, d4-MeOH): 8.47 (s, 1H), 8.14 (d, 1H), 7.73 (m, 2H), 7.49 (d, 1H), 7.15 (s, 1H), 4.24-4.13 (m, 2H), 4.09-3.97 (m, 5H), 3.76 (m, 1H), 3.22 (dd, 1H), 3.02-2.90 (m, 3H); MS (EI) for C20H20N4O3Cl2: 435 (MH+).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 min
  2. filtrationthe precipitate was filtered
  3. customdried
  4. dissolutionThe solid was dissolved in methanol (200 mL)
  5. additiontreated with Bio-Rad 1-X8 resin hydroxide form until pH 8
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-b1a31cb92069489db6976ddc2d8554db
Source dataset
uspto-grants-2009_08
Patent number
US07576074B2

Reaction notes

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