Triethylamine → HCID 58299649, compound

HRID 876058Notes

Reaction equation

HRID 876058 reaction equation
[CH3:1][N:2]1[CH2:7][C:6]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[O:5][CH2:4][CH2:3]1.[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=1.C(N(CC)CC)C>O1CCCC1>[Cl:13][C:14]1[N:15]=[N:16][C:17]([N:10]2[CH2:11][CH2:12][C:6]3([O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:7]3)[CH2:8][CH2:9]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 673313,6-DichloropyridazineHCID 217039594-Methyl-1-oxa-4,9-diazaspiro[5.5]undecane

Product 1

HCID 58299649HCID 58299649, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 405 (406.0 mg, 2.39 mmol) in tetrahydrofuran (17 mL) was added 3,6-dichloropyridazine (361.7 mg, 2.43 mmol), followed by triethylamine (0.680 mL, 4.89 mmol). The resulting solution was stirred at reflux for 38 hours. The reaction mixture was then concentrated and the residue was purified by reverse phase HPLC (acetonitrile/H2O containing 0.1% TFA each, 25 min from 10 to 40%) to give compound 406 as a sticky yellow solid (303 mg, 45%). LCMS-ESI (POS), M/Z, M+1: Found 283.1, Calculated 283.1.

Workup

  1. temperatureat reflux for 38 hours
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue was purified by reverse phase HPLC (acetonitrile/H2O containing 0.1% TFA each, 25 min from 10 to 40%)

Sources & evidence

ORD record
ord-971660201ade496f8b3a11592d2b1c43
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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