3-Methylbenzoic acid → Methyl 5-(N-{[6-amino-5-({3-[(3-methylbenzoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoate

HRID 1778141Notes

Reaction equation

HRID 1778141 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.[CH3:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](O)=[O:36]>>[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:35](=[O:36])[C:34]2[CH:38]=[CH:39][CH:40]=[C:32]([CH3:31])[CH:33]=2)[CH:25]=1

Participants

3

Reactant 2

HCID 74183-Methylbenzoic acidHCID 118130063Methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate

Product 1

HCID 91809241Methyl 5-(N-{[6-amino-5-({3-[(3-methylbenzoyl)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 3-methylbenzoic acid were coupled to give the title compound as a white foam (82 mg).

Sources & evidence

ORD record
ord-9821035b9b0e456e984f0c43f8296ad3
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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