Diisopropylethylamine → HCID 66885884, compound

HRID 2115578Notes

Reaction equation

HRID 2115578 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:20][N:21]([CH3:33])[C:22]1[CH:23]=[C:24]([NH:28][CH2:29][C:30]([OH:32])=O)[CH:25]=[CH:26][CH:27]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C.O>[CH3:33][N:21]([CH3:20])[C:22]1[CH:23]=[C:24]([NH:28][CH2:29][C:30]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)=[O:32])[CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 4723804N-(pyridin-2-ylmethyl)ethanamineHCID 66885914HCID 66885914, compound

Product 1

HCID 66885884HCID 66885884, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

A suspension of ethyl-pyridin-2-ylmethyl-amine (41.1 mmol) and DIPEA (112 mmol) in DMF (200 mL) was cooled to −20° C. and added to a cold (−20° C.) solution of (3-dimethylamino-phenylamino)-acetic acid (37.4 mmol) and TBTU (48.6 mmol) in DMF (300 mL). The reaction mixture was stirred for 10 min at −20° C. Water (500 mL) and ethyl acetate (500 mL) were added, the layers were separated and the organic layer washed with water (4×200 mL). The combined aqueous layers were extracted with ethyl acetate (300 mL). The combined organic layers were washed with NaOH solution (1.0 mol/L, 100 mL) and brine (100 mL) and dried over Na2SO4. The solvents were removed in vacuo and the obtained solid was dissolved in ethanol. A solution of hydrogen chloride in ether was added at 0° C., the solvents were removed and the residue was crystallized from ethanol/ether to give 7.6 g product as white crystals.

Workup

  1. customthe layers were separated
  2. washthe organic layer washed with water (4×200 mL)
  3. extractionThe combined aqueous layers were extracted with ethyl acetate (300 mL)
  4. washThe combined organic layers were washed with NaOH solution (1.0 mol/L, 100 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvents were removed in vacuo
  7. dissolutionthe obtained solid was dissolved in ethanol
  8. additionA solution of hydrogen chloride in ether was added at 0° C.
  9. customthe solvents were removed
  10. customthe residue was crystallized from ethanol/ether

Sources & evidence

ORD record
ord-302223575d4945d989f19da7f36d4e50
Source dataset
uspto-grants-2008_10
Patent number
US07435815B2

Reaction notes

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