Cyclohexylamine → HCID 33162899, compound

HRID 2367233Notes

Reaction equation

HRID 2367233 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:11])=O)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH:47]1([NH2:53])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>CN(C=O)C>[CH:47]1([NH:53][C:9]([C:6]2[CH:7]=[N:8][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:4][CH:5]=2)=[O:11])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 27775516-(Trifluoromethyl)nicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 33162899HCID 33162899, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-(trifluoromethyl)-3-pyridinecarboxylic acid (2.0 g, 10.5 mmol) in DMF (10 mL) was added HATU (4.18 g, 11.0 mmol) followed by Hunig's base (1.83 mL, 10.5 mmol). After 15 minutes, cyclohexylamine (2.40 mL, 20.9 mmol) was added, and the reaction mixture was stirred for 45 minutes at room temperature. The reaction was poured onto water (˜300 mL). After 5 minutes, the resulting aqueous mixture was filtered, and the white solid was air dried for ˜15 minutes to afford the title compound (2.57 g). LC-MS (ES) m/z=273 [M+H]+.

Workup

  1. additionThe reaction was poured onto water (˜300 mL)
  2. waitAfter 5 minutes
  3. filtrationthe resulting aqueous mixture was filtered
  4. customdried for ˜15 minutes

Sources & evidence

ORD record
ord-614642f187f64b84b436a6c59383eafd
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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