tert-Butylsulfonamide → 2-methyl-propane-2-sulfonic acid [5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide

HRID 593625Notes

Reaction equation

HRID 593625 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]#[N:21])=[C:7]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH:18]=O)[CH:17]=3)[N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH3:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])([CH3:25])[CH3:24]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]#[N:21])=[C:7]([C:12]3[CH:17]=[C:16]([CH2:18][NH:29][S:26]([C:23]([CH3:25])([CH3:24])[CH3:22])(=[O:28])=[O:27])[CH:15]=[N:14][CH:13]=3)[N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2757335tert-ButylsulfonamideHCID 582157716-chloro-2-(5-formyl-pyridin-3-yl)-1-methyl-1H-indole-3-carbonitrile

Product 1

HCID 582157772-methyl-propane-2-sulfonic acid [5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide

Procedure

6-Chloro-2-(5-formyl-pyridin-3-yl)-1-methyl-1H-indole-3-carbonitrile (Example 126) and 2-methyl-propane-2-sulfonic acid amide are processed according to the method described in Example 170 to give 2-methyl-propane-2-sulfonic acid [5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (s, 9H), 3.78 (s, 3H), 4.43 (d, J=6.1 Hz, 2H), 7.37 (dd, J=8.6, 1.8 Hz, 1H), 7.65 (t, J=6.2 Hz, 1H), 7.73 (d, J=8.3 Hz, 1H), 7.97 (d, J=1.5 Hz, 1H), 8.06 (t, J=2.1 Hz, 1H), 8.77 (d, J=1.8 Hz, 1H), 8.80 (d, J=2.0 Hz, 1H). HRMS (ESI) m/z 417.1150 [(M+H)+ Calcd for C20H21ClN4O2S: 417.1152].

Sources & evidence

ORD record
ord-8637f4b9e1814620a39a2acc414aa2ce
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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