N-Methyl-4-anisidine → HCID 59242118, compound

HRID 1876193Notes

Reaction equation

HRID 1876193 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:23])[CH:9]=2)[N:4]=1.ClC1C2C(=CC=C(F)C=2)N=C(CCl)[N:26]=1.COC1C=CC(NC)=CC=1>CC(O)C.Cl.C(Cl)Cl>[NH2:26][CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:23])[CH:9]=2)[N:4]=1

Participants

7

Reactant 3

HCID 22250N-Methyl-4-anisidineHCID 20094119HCID 20094119, compoundHCID 68517330HCID 68517330, compound

Product 1

HCID 59242118HCID 59242118, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

(2-Chloromethyl-6-fluoro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine: A suspension of 4-chloro-2-chloromethyl-6-fluoroquinazoline (265 mg, 1.15 mmol) and (4-methoxy-phenyl)-methyl-amine (175 mg, 1.26 mmol) in i-PrOH (10 mL) was treated with HCl (12 M, 4 drops) and stirred overnight at rt. The reaction was diluted with CH2Cl2 and washed with 5% NaOH. The organics were dried (MgSO4), concentrated and purified by gradient MPLC (SiO2, EtOAc/hexanes, 0-100%, 20 min) to provide 258 mg (68%) of the title compound. 1H NMR (DMSO-d6) δ 7.83 (dd, 1H), 7.62 (ddd, 1H), 7.25-7.33 (m, 2H), 7.02-7.10 (m, 2H), 6.47 (dd, 1H), 4.75 (s, 2H), 3.81 (s, 3H), 3.54 (s, 3H); LC-MS (ESI+; 332 ([M+H]+)).

Workup

  1. washwashed with 5% NaOH
  2. dry with materialThe organics were dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by gradient MPLC (SiO2, EtOAc/hexanes, 0-100%, 20 min)

Sources & evidence

ORD record
ord-1550491690ae4911a4121dc8a7569eff
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

Loading…