Potassium Carbonate → HCID 68516669, compound

HRID 1876228Notes

Reaction equation

HRID 1876228 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]([CH3:34])[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([CH2:22][N:23]3C(=O)C4C(=CC=CC=4)C3=O)[N:13]=2)[CH:5]=[C:6]([Cl:10])[C:7]=1[O:8][CH3:9].Cl.[Cl:36]CC1N=C(N(C2C=C(Cl)C(OC)=C(Cl)C=2)C)C2C(=CC=CC=2)N=1.C([O-])([O-])=O.[K+].[K+].C1(=O)NC(=O)C2=CC=CC=C12.[K]>CN(C=O)C.C(Cl)Cl.CCOC(C)=O>[ClH:1].[ClH:36].[NH2:23][CH2:22][C:14]1[N:13]=[C:12]([N:11]([C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[CH:5]=2)[CH3:34])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24194345Phthalimide potassium saltHCID 68514553HCID 68514553, compoundHCID 68519268HCID 68519268, compound

Product 1

HCID 68516669HCID 68516669, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

2-{4-[(3,5-Dichloro-4-methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-isoindole-1,3-dione: A mixture of (2-chloromethyl-quinazolin-4-yl)-(3,5-dichloro-4-methoxy-phenyl)-methyl-amine hydrochloride (521 mg, 1.24 mmol), K2CO3 (401 mg, 2.90 mmol) and potassium phthalimide (312 mg, 1.68 mmol) in DMF (7 mL) was heated at 50° C. for 4 h. EtOAc and DCM were added and this was washed with water then 50% satd NaCl then satd NaCl. The organic layer was dried (MgSO4), filtered through a pad of silica with an EtOAc wash then most of the solvents were removed on a rotary evaporator. The remaining solvent was removed from the crystalline material that had formed and the product was washed with two portions of EtOAc then suspended in hexanes, collected by filtration and washed with hexanes. The title compound was obtained as a paleyellow microcrystalline solid (373 mg; 61%). 1H NMR (CDCl3) δ 7.96-7.91 (m, 2H), 7.79-7.40 (m, 3H), 7.60 (m, 1H), 7.16-7.06 (m, 2H), 7.04 (s, 2H), 5.16 (s, 2H), 3.90 (s, 3H), 3.30 (s, 3H); LC-MS (ESI+; 493 ([M+H]+)).

Workup

  1. washthis was washed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered through a pad of silica with an EtOAc
  4. washwash
  5. custommost of the solvents were removed on a rotary evaporator
  6. customThe remaining solvent was removed from the crystalline material that
  7. customhad formed
  8. washthe product was washed with two portions of EtOAc
  9. filtrationcollected by filtration
  10. washwashed with hexanes

Sources & evidence

ORD record
ord-773eca4b5a0e4a96b4741b2577f4418e
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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