2,2,2-Trifluoroethanesulfonyl chloride → HCID 59534654, compound

HRID 1630912Notes

Reaction equation

HRID 1630912 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH3:21])[C:11]3[C:16]([C:17]=2[C:18]#[N:19])=[CH:15][CH:14]=[C:13]([Cl:20])[CH:12]=3)[CH:6]=[N:7][CH:8]=1.[F:22][C:23]([F:30])([F:29])[CH2:24][S:25](Cl)(=[O:27])=[O:26]>>[Cl:20][C:13]1[CH:12]=[C:11]2[C:16]([C:17]([C:18]#[N:19])=[C:9]([C:5]3[CH:4]=[C:3]([CH2:2][NH:1][S:25]([CH2:24][C:23]([F:30])([F:29])[F:22])(=[O:27])=[O:26])[CH:8]=[N:7][CH:6]=3)[N:10]2[CH3:21])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 58215751HCID 58215751, compound

Product 1

HCID 59534654HCID 59534654, compound

Procedure

2-(5-Aminomethyl-pyridin-3-yl)-6-chloro-1-methyl-1H-indole-3-carbonitrile (Example 186e) and 2,2,2-trifluoro-ethanesulfonyl chloride are processed according to the method described in Example 186f to give 2,2,2-trifluoro-ethanesulfonic acid [5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]amide. 1H NMR (400 MHz, MeOD) δ ppm 3.84 (s, 3H), 4.29 (q, J=9.6 Hz, 2H), 4.54 (s, 2H), 7.39 (dd, J=8.6, 1.8 Hz, 1H), 7.73 (d, J=8.3 Hz, 1H), 7.78 (d, J=1.8 Hz, 1H), 8.18 (t, J=2.0 Hz, 1H), 8.81 (d, J=2.0 Hz, 1H), 8.83 (d, J=2.0 Hz, 1H). HRMS (ESI) m/z 443.0557 [(M+H)+ Calcd for C18H15N4O2F3SCl: 443.0556].

Sources & evidence

ORD record
ord-548df977bc1046fe88b7e689354356b1
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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