Methanesulfonyl chloride → methanesulfonic acid [5-(1-methyl-1H-indol-2-yl)-pyridin-3-yl]-amide

HRID 593678Notes

Reaction equation

HRID 593678 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH3:17])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[N:6][CH:7]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>>[CH3:17][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:8]1[C:4]1[CH:3]=[C:2]([NH:1][S:19]([CH3:18])(=[O:21])=[O:20])[CH:7]=[N:6][CH:5]=1

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 582155792-(5-amino-pyridin-3-yl)-1-methyl-1H-indole

Product 1

HCID 59534662methanesulfonic acid [5-(1-methyl-1H-indol-2-yl)-pyridin-3-yl]-amide

Procedure

2-(5-amino-pyridin-3-yl)-1-methyl-1H-indole (Example 100) and methanesulfonyl chloride are processed according to the methods described in Example 225a and 225c to give methanesulfonic acid [5-(1-methyl-1H-indol-2-yl)-pyridin-3-yl]-amide. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.15 (s, 3H), 3.77 (s, 3H), 6.71 (s, 1H), 7.06-7.13 (m, 1H), 7.23 (ddd, J=8.2, 7.1, 1.1 Hz, 1H), 7.53 (d, J=7.6 Hz, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.79 (t, J=2.2 Hz, 1H), 8.48 (d, J=2.3 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H), 10.18 (s, 1H). HRMS: (ESI) m/z 302.0966 [(M+H)+ Calcd for C15H16N3O2S 302.0958].

Sources & evidence

ORD record
ord-011b2a85a46a4cbfa88d628dd0651fb8
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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