HCID 118162084, compound → HCID 118162099, compound

HRID 1749406Notes

Reaction equation

HRID 1749406 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][C@H:6]([NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11](S(C)=O)[N:10]=2)[CH2:5][CH2:4][C@@H:3]1[OH:22].[NH2:24][CH2:25][C:26]1[C:27]([C:34]([F:37])([F:36])[F:35])=[CH:28][C:29]([CH3:33])=[N+:30]([O-:32])[CH:31]=1>O1CCOCC1>[OH:22][C@H:3]1[CH2:4][CH2:5][C@@H:6]([NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]([NH:24][CH2:25][C:26]3[C:27]([C:34]([F:37])([F:35])[F:36])=[CH:28][C:29]([CH3:33])=[N+:30]([O-:32])[CH:31]=3)[N:10]=2)[CH2:7][C:2]1([CH3:23])[CH3:1]

Participants

4

Reactant 2

HCID 118162084HCID 118162084, compoundHCID 118162222HCID 118162222, compound

Product 1

HCID 118162099HCID 118162099, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (1S,4R)-2,2-dimethyl-4-((2-(methylsulfinyl)-5-(trifluoromethyl)pyrimidin-4-yl)amino)cyclohexanol (1.0 equiv.) and 5-(aminomethyl)-2-methyl-4-(trifluoromethyl)pyridine 1-oxide (1.0 equiv.) in dioxane (0.15 M) was heated at 110° C. for 14 h. Standard work-up afforded 5-(((4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)methyl)-2-methyl-4-(trifluoromethyl)pyridine 1-oxide (30% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 8.06 (s, 1H) 7.81-7.99 (m, 3H) 5.94-6.14 (m, 1H) 4.53 (m, 2H) 4.24-4.42 (m, 1H) 3.91 (m, 1H) 2.98-3.24 (m, 1H) 2.23-2.39 (m, 3H) 1.28-1.75 (m, 4H) 0.83-1.24 (m, 3H) 0.74 (s, 3H) 0.57 (s, 3H); MS(ESI) m/z 494.3[M+1]+.

Sources & evidence

ORD record
ord-fdc43f5a59a74a9081e07e2828caa4c8
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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