5-Amino-2-methylpyridine → (RS)-N-(Ethoxycarbonyl)-S-methyl-S-[3-({[4-(2-methyl-5-pyridylamino)-6-methoxyquinazolin-7-yl]oxy}methyl)phenyl]sulphoximide

HRID 249962

Reaction equation

HRID 249962 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:27])(=[N:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:20])[CH:14]=2)=[CH:5][C:4]=1[N:28]=[CH:29]N(C)C)#[N:2].[NH2:33][C:34]1[CH:35]=[CH:36][C:37]([CH3:40])=[N:38][CH:39]=1>ClCCl.CO>[CH2:25]([O:24][C:22]([N:21]=[S:19]([CH3:27])([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][O:11][C:6]2[CH:5]=[C:4]3[C:3]([C:1]([NH:33][C:34]4[CH:35]=[CH:36][C:37]([CH3:40])=[N:38][CH:39]=4)=[N:2][CH:29]=[N:28]3)=[CH:8][C:7]=2[O:9][CH3:10])[CH:14]=1)=[O:20])=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 2433135-Amino-2-methylpyridineHCID 57788001N'-(2-cyano-5-{3-[(RS)-N-(ethoxycarbonyl)-S-methylsulphonimidoyl]benzyloxy}-4-methoxyphenyl)-N,N-dimethylformimidamide

Product 1

HCID 57788021(RS)-N-(Ethoxycarbonyl)-S-methyl-S-[3-({[4-(2-methyl-5-pyridylamino)-6-methoxyquinazolin-7-yl]oxy}methyl)phenyl]sulphoximideYield 36%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

According to GWP 5, the reaction of N′-(2-cyano-5-{3-[(RS)-N-(ethoxycarbonyl)-S-methylsulphonimidoyl]benzyloxy}-4-methoxyphenyl)-N,N-dimethylformimidamide (100 mg, 0.22 mmol) with 5-amino-2-methylpyridine (28 mg, 0.26 mmol) and chromatography (silica gel, dichloromethane/methanol: 4/1) gives the desired product in 36% yield (40 mg).

Sources & evidence

ORD record
ord-bbafe1208a7f4645992b0e381f65f703
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Linked notes

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