3-Aminopyridine → (RS)-N-(Ethoxycarbonyl)-S-methyl-S-[3-({[4-(3-pyridylamino)quinazolin-7-yl]-amino}methyl)phenyl]sulphoximide

HRID 249957Notes

Reaction equation

HRID 249957 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:25])(=[N:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:18])[CH:12]=2)=[CH:5][C:4]=1[N:26]=[CH:27][N:28](C)[CH3:29])#N.[NH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.ClCCl.CO>CO>[CH2:23]([O:22][C:20]([N:19]=[S:17]([CH3:25])([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][NH:9][C:6]2[CH:5]=[C:4]3[C:3]([C:29]([NH:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)=[N:28][CH:27]=[N:26]3)=[CH:8][CH:7]=2)[CH:12]=1)=[O:18])=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 21226129Dichloromethane methanolHCID 57788040N'-(2-cyano-5-{3-[(RS)-N-(ethoxycarbonyl)-S-methylsulphonimidoyl]benzylamino}phenyl)-N,N-dimethylformimidamide

Product 1

HCID 57787978(RS)-N-(Ethoxycarbonyl)-S-methyl-S-[3-({[4-(3-pyridylamino)quinazolin-7-yl]-amino}methyl)phenyl]sulphoximideYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to GWP 5, the reaction of N′-(2-cyano-5-{3-[(RS)-N-(ethoxycarbonyl)-S-methylsulphonimidoyl]benzylamino}phenyl)-N,N-dimethylformimidamide (50 mg, 0.12 mmol) with 3-aminopyridine (14 mg, 0.14 mmol) and chromatographic purification (silica gel, dichloromethane/methanol: 0→30% methanol) gives the desired product in 68% yield (38 mg).

Sources & evidence

ORD record
ord-47ff968d437543bc942754fb411e8d0a
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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