Trifluoroacetic acid → HCID 178426444, compound

HRID 526467Notes

Reaction equation

HRID 526467 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][N:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][N:23]=3)[C:20]=2[OH:21])=[C:12]([CH3:31])[CH:11]=1)#[N:9].[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36][NH2:37]>>[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][N:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([NH:37][CH2:36][CH2:35][CH2:34][N:33]([CH3:38])[CH3:32])=[O:27])=[CH:24][N:23]=3)[C:20]=2[OH:21])=[C:12]([CH3:31])[CH:11]=1)#[N:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 178426451HCID 178426451, compound

Product 1

HCID 178426444HCID 178426444, compound

Procedure

The title compound, as a TFA salt, was prepared in a manner similar to Example 74 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and N1,N1-dimethylpropane-1,3-diamine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.81-2.01 (m, 2H) 2.44 (s, 3H) 2.80 (d, J=4.04 Hz, 6H) 3.13 (dt, J=10.36, 4.93 Hz, 2H) 3.37 (q, J=6.40 Hz, 2H) 7.67 (d, J=7.83 Hz, 1H) 7.74 (s, 1H) 7.79 (br. s., 1H) 8.22 (d, J=16.93 Hz, 1H) 8.43 (br. s., 1H) 8.86 (br. s., 1H) 8.93 (dd, J=2.15, 0.88 Hz, 1H) 9.38 (br. s., 1H) 13.25 (br. s., 1H). MS m/z [M+H]+ 405.2.

Sources & evidence

ORD record
ord-2191c5acffb24510a070c9fa674dffa3
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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