Diisopropylethylamine → HCID 59253661, compound

HRID 1258145Notes

Reaction equation

HRID 1258145 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[N:27]=[N:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C>ClCCl>[NH:15]1[CH2:16][CH2:17][CH:18]([NH:21][C:22]2[N:27]=[N:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 59253657HCID 59253657, compound

Product 1

HCID 59253661HCID 59253661, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-chloroethyl chloroformate (2.9 g, 20 mmol) was added dropwise to a stirring mixture of 6-(1-benzyl-piperidin-4-yl)-pyridazin-3-carbonitrile (D2) (1.5 g, 5.1 mmol) and diisopropylethylamine (2.6 g, 20 mmol) in dichloromethane (50 ml) at 0° C. The reaction mixture was stirred at room temperature for 2 h and then the solvent evaporated in vacuo. Methanol (50 ml) was added to the residue and the mixture was refluxed for 2 h. The solvent was evaporated in vacuo and the residue purified by column chromatography (silica gel; 5-12% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and the solvent evaporated in vacuo to yield D3 (0.9 g, 90%) as a solid. C10H13N5 requires 203. Found 204 (MH+)

Workup

  1. customthe solvent evaporated in vacuo
  2. additionMethanol (50 ml) was added to the residue
  3. temperaturethe mixture was refluxed for 2 h
  4. customThe solvent was evaporated in vacuo
  5. customthe residue purified by column chromatography (silica gel; 5-12% ammonia in methanol (7M)/dichloromethane)
  6. customThe desired fractions were collected
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-a2d46e0385f04511babd6850a7191407
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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