2-Fluoro-5-(trifluoromethyl)benzoic acid → Methyl 5-[N-({6-amino-5-[(3-{[2-fluoro-5-(trifluoromethyl)benzoyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate

HRID 1778142Notes

Reaction equation

HRID 1778142 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1.[F:31][C:32]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:33]=1[C:34](O)=[O:35]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:34](=[O:35])[C:33]2[CH:37]=[C:38]([C:41]([F:42])([F:43])[F:44])[CH:39]=[CH:40][C:32]=2[F:31])[CH:25]=1

Participants

3

Reactant 2

HCID 6882922-Fluoro-5-(trifluoromethyl)benzoic acidHCID 118130063Methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate

Product 1

HCID 118130082Methyl 5-[N-({6-amino-5-[(3-{[2-fluoro-5-(trifluoromethyl)benzoyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate

Procedure

In a manner similar to that described in Example 25, methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate and 2-fluoro-5-(trifluoromethyl)benzoic acid were coupled to give the title compound as a white foam (74 mg).

Sources & evidence

ORD record
ord-4b68c62f0a6e48d3ac8a8657352ceae9
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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