4-Chloro-3-(trifluoromethyl)benzoic acid → Methyl 5-[N-({6-amino-5-[(3-{[4-chloro-3-(trifluoromethyl)benzoyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate

HRID 1778144Notes

Reaction equation

HRID 1778144 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.[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][C:33]=1[C:41]([F:44])([F:43])[F:42]>>[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:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([Cl:31])=[C:33]([C:41]([F:44])([F:42])[F:43])[CH:34]=2)[CH:25]=1

Participants

3

Reactant 2

HCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 118130063Methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate

Product 1

HCID 118130099Methyl 5-[N-({6-amino-5-[(3-{[4-chloro-3-(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 4-chloro-3-(trifluoromethyl)benzoic acid were coupled to give the title compound as a white solid (74 mg).

Sources & evidence

ORD record
ord-8880329f40254a6092ae7c379800a731
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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