Triethylamine → HCID 67996338, compound

HRID 659628Notes

Reaction equation

HRID 659628 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH:19]([C:23](O)=[O:24])[CH2:18]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[NH:26]([CH3:28])[CH3:27].Cl.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.[Cl-].[Na+].O.CO.C(Cl)Cl>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH:19]([C:23]([N:26]([CH3:28])[CH3:27])=[O:24])[CH2:18]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54793657HCID 54793657, compound

Product 1

HCID 67996338HCID 67996338, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 100-mL 3-necked round-bottomed flask was charged with a solution of 1-((9-ethyl-9H-carbazol-3-yl)methyl)piperidine-3-carboxylic acid (1 g, 2.98 mmol, 1.00 equiv) in DMF (50 mL), followed by HNMe2.HCl (723 mg, 8.93 mmol, 3.00 equiv) and triethylamine (1.2 g, 11.88 mmol, 4.00 equiv) at 0° C. To this mixture was added HATU (1.13 g, 2.97 mmol, 1.00 equiv) at 0° C. The resulting mixture was stirred at room temperature for 16 hours. The reaction progress was monitored by TLC (DCM:MeOH=10:1). Upon completion, the resulting mixture was diluted with brine (30 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (100:1) affording 1-((9-ethyl-9H-carbazol-3-yl)methyl)-N,N-dimethylpiperidine-3-carboxamide as a white solid (0.8 g, 74%). LCMS: [M+H]+: 364. 1H NMR (CDCl3, 300 MHz) δ 8.17 (t, 2H), 7.44 (m, 4H), 7.30 (t, 1H), 4.35 (m, 4H), 3.28 (m, 4H), 3.06 (s, 3H), 2.94 (d, 3H), 2.35 (s, 2H), 1.85 (m, 3H), 1.42 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered off
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluted with dichloromethane/methanol (100:1)

Sources & evidence

ORD record
ord-b9f01e6f970a411ab2d5f6e853563a6a
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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