3,6-Dichloropyridazine → HCID 86710542, compound

HRID 1027147Notes

Reaction equation

HRID 1027147 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([NH2:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=1>C(O)CCC>[Cl:13][C:14]1[N:15]=[N:16][C:17]([NH:10][CH:5]2[CH2:6][C:7]([CH3:8])([CH3:9])[N:2]([CH3:1])[C:3]([CH3:12])([CH3:11])[CH2:4]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 673313,6-DichloropyridazineHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidine

Product 1

HCID 86710542HCID 86710542, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 1,2,2,6,6-pentamethylpiperidin-4-amine (14.2 g, 83 mmol) and 3,6-dichloropyridazine (6.2 g, 41.6 mmol) in n-butanol (10 mL) was heated at 120° C. for 120 min. The crude material solidified and was re-suspended in n-butanol (15 mL) and heated at 120° C. for 1 h. This crude material was combined with batch 1 for workup and purification. Water and CH2Cl2 were added to the combined crude material and the organic layer was separated, washed with water and brine, dried over MgSO4, filtered and concentrated. The crude material was recyrstallized from CH3CN (400 mL) to give 6-chloro-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyridazin-3-amine, Intermediate 1-5 (15.5 g, first crop). Recrystallization was repeated using CH3CN to give a 2nd crop of 6-chloro-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyridazin-3-amine Intermediate 1-5 (3.98 g). LCMS Rt=1.10 min (condition B); MS (M+1)=283.0. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.15 (d, J=9.3 Hz, 1H), 6.65 (d, J=9.3 Hz, 1H), 4.70 (d, J=7.3 Hz, 1H), 4.08-4.26 (m, 1H), 2.31 (s, 3H), 1.89-2.09 (m, 2H), 1.42 (apparent t, J=12.1 Hz, 2H), 1.21 (s, 6H), 1.15 (s, 6H).

Workup

  1. temperatureheated at 120° C. for 1 h
  2. customThis crude material was combined with batch 1 for workup and purification
  3. additionWater and CH2Cl2 were added to the
  4. customthe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9ed019ee86d84dcca68de812f946b3bd
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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