Sodium → 1-{2-[4-(3-Ethynyl-phenylamino)-7-(2-methoxy-ethoxy)-quinazolin-6-yloxy]-ethyl}-1H-pyridin-4-one Hydrochloride

HRID 1869097Notes

Reaction equation

HRID 1869097 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[CH:29])[CH:23]=1.[Na].[N:31]1[CH:36]=[CH:35][C:34](=[O:37])[CH2:33][CH:32]=1>CO.C(Cl)(Cl)Cl>[ClH:2].[C:28]([C:24]1[CH:23]=[C:22]([NH:21][C:9]2[C:8]3[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:6]([O:5][CH2:4][CH2:3][N:31]4[CH:36]=[CH:35][C:34](=[O:37])[CH:33]=[CH:32]4)[CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:27]=[CH:26][CH:25]=1)#[CH:29]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 17984897Piridin-4-oneHCID 189250626-O-Desmethoxyethyl-6-O-chloroethyl Erlotinib Hydrochloride

Product 1

HCID 189250441-{2-[4-(3-Ethynyl-phenylamino)-7-(2-methoxy-ethoxy)-quinazolin-6-yloxy]-ethyl}-1H-pyridin-4-one Hydrochloride

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

The free base of this product was prepared from the title product of Example 30 and the sodium salt of pyrid-4-one as described for Example 50. The free base was isolated by flash chromatography with 15% methanol/CHCl3 and converted to the title product according to the procedure described for Example 28 (32%; M.P. 155°-168° C. (dec); LC-MS: 457 (MH+); anal. RP-HPLC RT: 3.45 min).

Sources & evidence

ORD record
ord-c8f693869f4a4d07a0f7b4527e1ba1d2
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

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