3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid → HCID 11315984, compound

HRID 2354762Notes

Reaction equation

HRID 2354762 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].[CH3:11][CH:12]([CH3:30])[CH2:13][CH2:14][NH:15][C:16]([C:18]1[N:19]=[N:20][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:22][CH:23]=1)=[O:17]>>[CH:12]1([CH2:13][CH2:14][NH:15][C:16]([C:18]2[N:19]=[N:20][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])[CH2:26][CH2:25]3)=[CH:22][CH:23]=2)=[O:17])[CH2:30][CH2:11]1

Participants

3

Reactant 2

HCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 668493226-Piperazin-1-yl-pyridazin-3-carboxylic acid (3-methylbutyl)amide

Product 1

HCID 11315984HCID 11315984, compound

Procedure

Following the procedure of Example 14, making variations only as required to use 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid in place of 4,4,4-trifluoro-2-methylbutyric acid to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-methylbutyl)amide, the title compound was obtained as a white solid (55% yield). m.p. 181-183° C. 1H NMR (300 MHz, CDCl3) δ 8.07, 7.98, 7.01, 4.86, 3.92-3.81, 3.55, 1.74, 1.51, 0.81-0.68, 0.46, 0.09. 13C NMR (75 MHz, CDCl3) δ 167.2, 163.1, 160.0, 145.4, 127.1, 126.3, 122.5, 112.5. 76.8-75.6 (q, J=117 Hz, C-19F), 44.6, 39.7, 35.3, 20.5, 8.5, 4.8. MS (ES+) m/z 416 (M+1).

Sources & evidence

ORD record
ord-588e1bfe1e5540b59a47fce8a13506d7
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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