N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide → (S)-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinamide

HRID 607466Notes

Reaction equation

HRID 607466 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:29]=1)[C:7]([N:9]=[S@@:10]([CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[C:30]([C:32]1[CH:33]=[C:34]([NH:38][C:39]([C:41]2[N:45]([CH3:46])[N:44]=[C:43]([CH3:47])[CH:42]=2)=[O:40])[CH:35]=[CH:36][CH:37]=1)#[CH:31]>>[Si:22]([O:21][CH2:20][CH2:19][CH2:18][S@:10](=[O:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N:9][C:7](=[O:8])[C:6]1[CH:29]=[C:2]([C:31]#[C:30][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([NH:38][C:39]([C:41]3[N:45]([CH3:46])[N:44]=[C:43]([CH3:47])[CH:42]=3)=[O:40])[CH:33]=2)[CH:3]=[N:4][CH:5]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 57657904N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideHCID 86629482(S)-5-bromo-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]nicotinamide

Product 1

HCID 57657857(S)-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinamide

Procedure

In a manner similar to that described in Example 506 (step 3), (S)-5-bromo-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]nicotinamide and N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide are converted to the title compound.

Sources & evidence

ORD record
ord-7caacd93a0ea4f6082b89beece6787ab
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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