Triethylamine → HCID 58180914, compound

HRID 1772846Notes

Reaction equation

HRID 1772846 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[C:12]([F:19])[CH:11]=1)#[N:9].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[CH3:44][C@H:45]1[NH:50][CH2:49][CH2:48][N:47]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:46]1>C1COCC1.O.C(OCC)(=O)C>[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:50]2[CH2:49][CH2:48][N:47]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:46][C@H:45]2[CH3:44])=[O:16])=[C:12]([F:19])[CH:11]=1)#[N:9]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5906594-Cyano-2-fluorobenzoic acidHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58180914HCID 58180914, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (803 μL, 5.76 mmol) was added to a mixture of 4-cyano-2-fluorobenzoic acid (247 mg, 1.50 mmol, Alfa Aesar) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (522 mg, 1.37 mmol) in THF (11 mL). After stirring for 15 min, tert-butyl (3R)-3-methylpiperazine-1-carboxylate (0.25 g, 1.2 mmol, Aldrich) was added. The mixture was stirred for 3 h. Ethyl acetate and water were added, shaken and the layers separated. The organic layer was washed with water, 0.1N NaOH, and brine; dried over sodium sulfate, decanted and concentrated to afford product which was used without further purification (450 mg, 100%). 1H NMR (400 MHz, CDCl3, rotamers): δ 7.57-7.40 (m, 3H), 4.98-2.63 (m, 7H), 1.47 (s, 9H), 1.28 (d, 1.8H), 1.19 (br s, 1.2H); LCMS (M-tBu+2H)+: 292.1.

Workup

  1. stirringThe mixture was stirred for 3 h
  2. stirringshaken
  3. customthe layers separated
  4. washThe organic layer was washed with water, 0.1N NaOH, and brine
  5. dry with materialdried over sodium sulfate
  6. customdecanted
  7. concentrationconcentrated
  8. customto afford product which
  9. customwas used without further purification (450 mg, 100%)

Sources & evidence

ORD record
ord-63787c0921e547578a27e5e2379c4dfa
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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