Diisopropylethylamine → HCID 57106292, compound

HRID 2209273Notes

Reaction equation

HRID 2209273 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([I:8])=[CH:6][CH:7]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C>CC(O)(C)C>[I:8][C:5]1[N:4]=[N:3][C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 154188393-Chloro-6-iodopyridazine

Product 1

HCID 57106292HCID 57106292, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

3-chloro-6-iodopyridazine (510 mg, 2.1 mmol) and tert-butyl piperazine-1-carboxylate (415 mg, 2.23 mmol) were taken up in tBuOH (8 mL). iPr2NEt (480 μL, 2.8 mmol) was added and the stirred reaction mixture was heated to 100° C. After 48 h, the reaction mixture was cooled and was partitioned between EtOAc and water. The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-25% Et2O in DCM) to afford tert-butyl 4-(6-iodopyridazin-3-yl)piperazine-1-carboxylate 7.12. LCMS-ESI+ (m/z): [M+H—CO2tBu]+ calcd for C8H121 N4: 291.0; found: 291.0.

Workup

  1. customthe stirred reaction mixture
  2. temperaturethe reaction mixture was cooled
  3. customwas partitioned between EtOAc and water
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica gel chromatography (0-25% Et2O in DCM)

Sources & evidence

ORD record
ord-ca82a9e9fe9040549862b21638b5b72f
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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