Benzenamine, 3-ethynyl- → 6-O-Desmethoxyethyl-6-O-chloroethyl Erlotinib Hydrochloride

HRID 1288875Notes

Reaction equation

HRID 1288875 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:9]([O:12][CH2:13][CH2:14][Cl:15])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:21]([C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26])#[CH:22]>>[ClH:1].[Cl:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:5]=[CH:4][N:3]=[C:2]2[NH:26][C:25]1[CH:27]=[CH:28][CH:29]=[C:23]([C:21]#[CH:22])[CH:24]=1

Participants

3

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 189250244-Chloro-6-(2-chloroethoxy)-7-(2-methoxyethoxy)quinazoline

Product 1

HCID 189250626-O-Desmethoxyethyl-6-O-chloroethyl Erlotinib Hydrochloride

Procedure

The title product was prepared from 4-chloro-6-(2-chloro-ethoxy)-7-(2-methoxyethoxy)-quinazoline (399 mg, 1.26 mmol) and 3-ethynyl-aniline (147 mg, 1.26 mmol) as described for Example 29. (515 mg; 94%; M.P. 215°-225° C. (dec); LC-MS: 398 (MH+); anal. RP18-HPLC RT: 4.85 min.).

Sources & evidence

ORD record
ord-d8d50823c5d147d28ee59055547e9b35
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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