Methyl 3-[4-(S-methylsulfonimidoyl)phenyl]propanoate → Methyl 3-{4-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}propanoate

HRID 391588Notes

Reaction equation

HRID 391588 reaction equation
[NH2:1][C:2]1[C:10]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([C:22]3[N:23]([CH3:28])[N:24]=[C:25]([CH3:27])[CH:26]=3)=[O:21])[CH:14]=2)=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])=[CH:35][CH:34]=1)(=[NH:32])=[O:31]>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:32]=[S:30]([C:33]2[CH:34]=[CH:35][C:36]([CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:38]=2)([CH3:29])=[O:31])=[O:8])=[CH:9][C:10]=1[C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([C:22]2[N:23]([CH3:28])[N:24]=[C:25]([CH3:27])[CH:26]=2)=[O:21])[CH:14]=1

Participants

3

Reactant 2

HCID 57657822Methyl 3-[4-(S-methylsulfonimidoyl)phenyl]propanoateHCID 576578676-Amino-5-{3-[(2,5-dimethyl-2H-pyrazole-3-carbonyl)-amino]-phenylethynyl}-nicotinic acid

Product 1

HCID 24956709Methyl 3-{4-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}propanoateYield 42%

Procedure

In a manner similar to that described in Example 480 (step 6), 6-Amino-5-{3-[(2,5-dimethyl-2H-pyrazole-3-carbonyl)-amino]-phenylethynyl}-nicotinic acid (0.250 g, 0.666 mmol) and methyl 3-(4-(S-methylsulfonimidoyl)-phenyl)propanoate (0.160 g, 0.666 mmol) were reacted to give the title compound (0.167 g, 42%)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-70ae11221e7e44bb9b4de20764a9904f
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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