Diisopropylethylamine → HCID 118162088, compound

HRID 1749426Notes

Reaction equation

HRID 1749426 reaction equation
CCN(C(C)C)C(C)C.Cl[C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:14]=[C:13]([NH:21][CH2:22][C:23]2[CH:24]=[N+:25]([O-:33])[CH:26]=[CH:27][C:28]=2[C:29]([F:32])([F:31])[F:30])[N:12]=1.[NH2:34][CH:35]1[C:38]([CH3:40])([CH3:39])[CH:37]([OH:41])[C:36]1([CH3:43])[CH3:42]>C(O)C>[OH:41][CH:37]1[C:38]([CH3:40])([CH3:39])[CH:35]([NH:34][C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:14]=[C:13]([NH:21][CH2:22][C:23]3[CH:24]=[N+:25]([O-:33])[CH:26]=[CH:27][C:28]=3[C:29]([F:32])([F:31])[F:30])[N:12]=2)[C:36]1([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 203376Cyclobutanol, 3-amino-2,2,4,4-tetramethyl-HCID 118162206HCID 118162206, compound

Product 1

HCID 118162088HCID 118162088, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

DIEA (3.0 equiv.) was placed in a sealable flask with 3-(((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)methyl)-4-(trifluoromethyl)pyridine 1-oxide (1.0 equiv.), 3-amino-2,2,4,4-tetramethylcyclobutanol (2.0 equiv.)(See J. Med. Chem. 2011, 54, 7693-7704 for preparation), and ethanol. The flask was purged with nitrogen and sealed. The reaction mixture was heated to 80° C. for 9 h. Standard work-up afforded the following compounds. Stereochemistry was assigned based on similar activity as other compounds provided herein in the biochemical assays described herein.

Workup

  1. customThe flask was purged with nitrogen
  2. customsealed
  3. customStandard work-up afforded the following compounds
  4. customprovided herein in the biochemical

Sources & evidence

ORD record
ord-b59e146ce71b4ce4a7460e15367a5b7d
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

Loading…