Triethylamine → HCID 21071120, compound

HRID 1372021Notes

Reaction equation

HRID 1372021 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N:14]([CH2:17][C:18]1[N:22]([CH2:23][C:24](O)=[O:25])[N:21]=[C:20]([C:27]([F:30])([F:29])[F:28])[C:19]=1[Cl:31])=[N+:15]=[N-:16].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[N:14]([CH2:17][C:18]1[N:22]([CH2:23][C:24]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)=[O:25])[N:21]=[C:20]([C:27]([F:30])([F:28])[F:29])[C:19]=1[Cl:31])=[N+:15]=[N-:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 974781-(4-Chlorophenyl)piperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210711575-(Azidomethyl)-4-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid

Product 1

HCID 21071120HCID 21071120, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 2.71 g (13.7 mmol) of 1-(4-Chlorophenyl)piperazine and 3.58 g (12.5 mmol) of (5-Azidomethyl-4-chloro-3-trifluoromethyl-pyrazol-1-yl)-acetic acid in 40 mL of anhydrous dimethylformamide was added 4.36 mL (31.2 mmol) of triethylamine. The solution was cooled to 0° C., and 5.21 g (13.7 mmol) of O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) was added. After 2 hours the reaction was diluted with two volumes of water, and the solvent was decanted away from the resulting oil. The oil was crystallized by dissolving in methanol and adding water in small portions. The product was isolated as a white solid by filtration: 1H NMR (DMSO-d6, 400 MHz) 7.23 (d, 2H), 6.97 (d, 2H), 5.48 (s, 2H), 4.62 (s, 2H), 3.60 (m, 4H), 3.24 (m, 2H), 3.12 (m, 2H) ppm; MS (ES) M+H expected=462.1, found=462.0.

Workup

  1. customthe solvent was decanted away from the resulting oil
  2. customThe oil was crystallized
  3. dissolutionby dissolving in methanol
  4. additionadding water in small portions
  5. customThe product was isolated as a white solid by filtration

Sources & evidence

ORD record
ord-014e1e02a6f043ef9c8bc84f3f665156
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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