Monoethyl oxalate → 3-Amino-N-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)propanamide

HRID 1675202Notes

Reaction equation

HRID 1675202 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([NH:28][C:29](=[O:38])[CH2:30][CH2:31][NH:32]C(=O)COC)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.C(OC(=O)C(O)=O)C>>[NH2:32][CH2:31][CH2:30][C:29]([NH:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][N:19]=[C:18]2[NH:17][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:2]([Cl:1])[CH:3]=1)=[O:38]

Participants

3

Reactant 2

HCID 74701Monoethyl oxalateHCID 11562882N-{4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-3-(2-methoxy-acetylamino)-propionamide

Product 1

HCID 673341233-Amino-N-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)propanamide

Procedure

The procedure of (20-2) of Example 20 was repeated except for using oxalic acid monoethylester and 0.09 g of the compound obtained in (20-1) of Example 20 instead of methoxyacetic acid, and subjecting column chromatography (eluent-chloroform:methanol=15:1) to obtain the title compound (0.04 g, 37%).

Sources & evidence

ORD record
ord-0a2ac6a4a9084a5ca1af7f0982af2f9e
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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