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 607437Notes

Reaction equation

HRID 607437 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11]([CH3:23])(=[N:13][C:14]([C:16]2[CH:17]=[N:18][CH:19]=[C:20](Br)[CH:21]=2)=[O:15])=[O:12])[CH:6]=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]>>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11]([CH3:23])(=[N:13][C:14]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([C:26]#[C:25][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]4[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=4)=[O:35])[CH:28]=3)[CH:21]=2)=[O:15])=[O:12])[CH:6]=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-bb79c7961be747f68f1a3d8891399cb2
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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