Diisopropylethylamine → HCID 86675756, compound

HRID 571528Notes

Reaction equation

HRID 571528 reaction equation
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[N:12]=[CH:13][C:14]([C:17]([OH:19])=O)=[N:15][CH:16]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[F:44][C:45]([F:51])([F:50])[C:46]1([NH2:49])[CH2:48][CH2:47]1.C([O-])(O)=O.[Na+]>>[Cl:10][C:11]1[N:12]=[CH:13][C:14]([C:17]([NH:49][C:46]2([C:45]([F:51])([F:50])[F:44])[CH2:48][CH2:47]2)=[O:19])=[N:15][CH:16]=1

Participants

6

Reactant 5

HCID 81531DiisopropylethylamineHCID 4654725-Chloropyrazinoic acidHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 116511971-(Trifluoromethyl)cyclopropanamine

Product 1

HCID 86675756HCID 86675756, compoundYield 67%

Procedure

N,N-Diisopropylethylamine (1.3 mL, 7.5 mmol) was added to a mixture of 5-chloropyrazine-2-carboxylic acid (0.40 g, 2.5 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.0 g, 2.8 mmol) and 1-(trifluoromethyl)cyclopropanamine (0.32 g, 2.5 mmol) (Oakwood, Cat. #: 038175) in dichloromethylene (10 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was worked up with saturated aqueous NaHCO3, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-20%) to afford the desired product (0.41 g, 67%). LCMS (M+H)+: m/z=266.0/267.9.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-20%)

Sources & evidence

ORD record
ord-644d2fb278fc47b79cc51e65dc75eea5
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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