4-ethoxy-2-fluoroaniline → HCID 59242016, compound

HRID 1876213Notes

Reaction equation

HRID 1876213 reaction equation
Cl.ClCC1N=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][C:16]=2[F:24])C2C(=CC=CC=2)N=1.Cl[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([CH2:36]Cl)[N:27]=1.C(OC1C=CC([NH2:47])=C(F)C=1)C>C(O)(C)C.Cl>[NH2:47][CH2:36][C:28]1[N:27]=[C:26]([N:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][C:16]=2[F:24])[CH3:12])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1

Participants

6

Reactant 3

HCID 37344624-ethoxy-2-fluoroanilineHCID 131575204-Chloro-2-(chloromethyl)quinazolineHCID 68519575(2-Chloromethyl-quinazolin-4-yl)-(4-ethoxy-2-fluoro-phenyl)-amine hydrochloride

Product 1

HCID 59242016HCID 59242016, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

(2-Chloromethyl-quinazolin-4-yl)-(4-ethoxy-2-fluoro-phenyl)-amine hydrochloride: To 4-chloro-2-chloromethyl-quinazoline (500 mg, 2.3 mmol) dissolved in isopropanol (7.6 mL) was added 4-ethoxy-2-fluoro-phenylamine (540 mg, 2.8 mmol) and HCl (12 M, 1 drop). The reaction was stirred overnight at room temperature. The resulting precipitate was filtered to give 613 mg of the title compound. 1H NMR (DMSO-d6) δ 8.76 (d, 1H), 8.1 (t, 1H), 7.98 (d 1H), 7.85 (t, 1H), 7.47 (t 1H), 7.04 (d, 1H), 6.90 (d, 1H), 4.75 (s, 2H), 4.1 (q, 2H), 1.36 (t, 3H); LC-MS (ESI+; 351 ([M+H]+)).

Workup

  1. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-70c5cc815024442885fa41608ef725c4
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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