Water → HCID 58045831, compound

HRID 657893Notes

Reaction equation

HRID 657893 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].Br.Cl[C:10]1[C:11]2[CH2:22][CH2:21][CH2:20][C:12]=2[C:13]2[N:14]([C:16]([NH2:19])=[N:17][N:18]=2)[N:15]=1.O>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:10]2[C:11]3[CH2:22][CH2:21][CH2:20][C:12]=3[C:13]3[N:14]([C:16]([NH2:19])=[N:17][N:18]=3)[N:15]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 86650799HCID 86650799, compound

Product 1

HCID 58045831HCID 58045831, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

Cyclopropylmethanol (1.78 ml) was initially charged in DMF (25 ml). Subsequently, the mixture was admixed with sodium hydride (541 mg) under argon and stirred at 45° C. for 0.5 h. Subsequently, 6-chloro-8,9-dihydro-7H-cyclopenta[d][1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.017, 1.31 g) was dissolved in DMF (20 ml) and 11.25 ml of the alkoxide solution were added in portions at 45° C. over 90 min. Then the mixture was stirred at 45° C. for another hour. After adding a little water, the mixture was dried and purified using silica gel (80 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min). 528 mg of the title compound were obtained. LC-MS rt: 0.63 min [M+H]+: 246.1 (met. b)

Workup

  1. stirringThen the mixture was stirred at 45° C. for another hour
  2. customthe mixture was dried
  3. custompurified
  4. customsilica gel (80 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min)

Sources & evidence

ORD record
ord-6e53d53efb6443d4975d5447b0d3c666
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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