Diisopropylethylamine → HCID 178461513, compound

HRID 730757Notes

Reaction equation

HRID 730757 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][C:9]([N:11]3[CH2:16][CH2:15][NH:14][C@H:13]([CH3:17])[CH2:12]3)=[N:10][C:6]=2[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.Cl[C:23]1[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(C(C)C)CC)(C)C>O>[Cl:1][C:2]1[C:7]2[NH:8][C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:23]4[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][N:24]=4)[C@H:13]([CH3:17])[CH2:12]3)=[N:10][C:6]=2[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 178461512HCID 178461512, compound

Product 1

HCID 178461513HCID 178461513, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of the piperazine from step (a) above (80 mg, 0.25 mmol), 2-chloro-3-trifluoromethyl-pyridine (54 mg, 0.3 mmol, Aldrich) and NAN-diisopropylethylamine (0.5 mL, 2.9 mmol, Aldrich) was heated in a microwave synthesizer for 120 min at 250° C. Water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 35% EtOAc/hexane to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 464 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic phases were washed with brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with 35% EtOAc/hexane

Sources & evidence

ORD record
ord-82cc65b4061249eca784c836b58739ad
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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