N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide → methyl{3-[N-({5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetate

HRID 391595

Reaction equation

HRID 391595 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([N:10]=[S:11]([C:14]2[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=2)([CH3:13])=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=1.[C:25]([C:27]1[CH:28]=[C:29]([NH:33][C:34]([C:36]2[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=2)=[O:35])[CH:30]=[CH:31][CH:32]=1)#[CH:26]>>[CH3:41][N:40]1[C:36]([C:34]([NH:33][C:29]2[CH:28]=[C:27]([C:25]#[C:26][C:2]3[CH:3]=[C:4]([C:8]([N:10]=[S:11]([C:14]4[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=4)([CH3:13])=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=3)[CH:32]=[CH:31][CH:30]=2)=[O:35])=[CH:37][C:38]([CH3:42])=[N:39]1

Participants

3

Reactant 2

HCID 57657904N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideHCID 57657931Methyl (3-{N-[(5-bromopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}phenyl)acetate

Product 1

HCID 57657926methyl{3-[N-({5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetate

Procedure

In a manner similar to that described in Example 460, methyl (3-{N-[(5-bromopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}phenyl)acetate (202 mg, 0.492 mmol) and N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (153 mg, 0.64 mmol), were converted to the title compound as a light yellow solid foam (275 mg, 98%).

Sources & evidence

ORD record
ord-0e0b99c3d076441f885ed4bac8624917
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Linked notes

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