Trifluoroacetic acid → HCID 178426440, compound

HRID 578971Notes

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][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][N:34]1[CH2:39][CH2:40][CH2:41][NH2:42]>>[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:42][CH2:41][CH2:40][CH2:39][N:34]4[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]4[CH3:32])=[O:27])=[CH:24][N:23]=3)[C:20]=2[OH:21])=[C:12]([CH3:31])[CH:11]=1)#[N:9]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 5202111-(3-Aminopropyl)-2-pipecoline

HCID 178426451HCID 178426451, compound

Product 1

HCID 178426440HCID 178426440, 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 3-(2-methylpiperidin-1-yl)propan-1-amine 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20-1.32 (m, 3 H) 1.38-1.55 (m, 2 H) 1.56-1.74 (m, 2 H) 1.74-2.06 (m, 4 H) 2.40-2.47 (m, 3 H) 2.91-3.16 (m, 2 H) 3.16-3.34 (m, 2 H) 3.35-3.69 (m, 3 H) 7.63-7.70 (m, 1 H) 7.72-7.86 (m, 2H) 8.20 (br. s., 1 H) 8.42 (d, J=7.33 Hz, 2 H) 8.85-9.00 (m, 2 H) 9.03-9.38 (m, 1 H) 12.63-13.81 (m, 1 H). MS m/z [M+H]+ 459.2.

Sources & evidence

ORD record: ord-b53f7a12eae84c19b4c3dd3b6fd5f6d7
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040522B2

Reaction notes

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