Triethylamine → HCID 59262192, compound

HRID 534790Notes

Reaction equation

HRID 534790 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.[CH3:22][C@H:23]1[CH2:28][N:27]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([NH:36][CH3:37])=[CH:32][CH:31]=2)[CH2:26][CH2:25][N:24]1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:22][C@H:23]1[CH2:28][N:27]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]([CH3:37])[C:15]([C:14]3[CH:18]=[CH:19][C:11]([C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:21])([F:20])[F:1])=[CH:4][CH:5]=4)=[O:10])=[CH:12][CH:13]=3)=[O:16])=[CH:32][CH:31]=2)[CH2:26][CH2:25][N:24]1[C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23652403HCID 23652403, compoundHCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

Product 1

HCID 59262192HCID 59262192, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

The acid chloride from step 1 was taken up in DCM (2 mL) and added drop-wise to a mixture of 1,1-dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate (D3) (0.170 g, 0.53 mmol) and triethylamine (0.11 mL) in DCM (2 mL). The reaction mixture was stirred at room temperature under argon overnight then diluted with water (20 mL) and DCM (20 mL). The aqueous layer was extracted with DCM (20 mL) and the combined organic layers were dried, concentrated and purified by column chromatography. Elution with 0-30% EtOAc/pentane gave the title compound as a colourless oil (0.244 g). MS (ES): MH+ 596.2.

Workup

  1. additionadded drop-wise
  2. extractionThe aqueous layer was extracted with DCM (20 mL)
  3. customthe combined organic layers were dried
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. washElution with 0-30% EtOAc/pentane

Sources & evidence

ORD record
ord-a0a503a0bcda40eaa10ec8392a2668b5
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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