Hydrazine hydrate (1:1) → HCID 77967101, compound

HRID 1878573Notes

Reaction equation

HRID 1878573 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:22]=3)[CH:16]=[C:4]2[N:3]=1.O.[NH2:30][NH2:31].O1[CH2:37][CH2:36]OCC1>>[CH3:4][C:16]1[CH:15]=[C:17]([CH:22]=[CH:36][CH:37]=1)[CH:18]=[N:30][NH:31][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:22]=3)[CH:16]=[C:4]2[N:3]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)2×HCID 312751,4-DioxaneHCID 86659726HCID 86659726, compound

Product 1

HCID 77967101HCID 77967101, compound

Conditions

Temperature
60 °C

Procedure

There was suspended, in 1,4-dioxane (3 mL), 5-chloro-7-morpholin-4-yl-2-(6-morpholin-4-yl-pyridin-3-yl)-pyrazolo[1,5-a]pyrimidine (28.9 mg, 0.0720 mM) and then hydrazine monohydrate (34.8 μL, 0.720 mM) was added to the suspension. After stirring this suspension at 60° C. overnight, it was stirred at 150° C. for 10 minutes under the irradiation with microwaves. Hydrazine monohydrate (40 μL, 0.82 mM) was added to this reaction liquid and then it was stirred at 150° C. for 15 minutes under the irradiation with microwaves. This reaction liquid was diluted with a saturated aqueous common salt solution and then extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate and the solvent was distilled off. The resulting residue was suspended in ethanol (2 mL), then acetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (8.5 μL, 0.072 mM) were added to the suspension and the mixture was stirred at room temperature for one hour. The solvent was distilled off from the reaction mixture, the resulting residue was purified by the reversed phase HPLC and then subjected to a desalting operation to thus give the title compound (14.3 mg, overall yield of these two steps: 40%).

Workup

  1. stirringwas stirred at 150° C. for 10 minutes under the irradiation with microwaves
  2. stirringit was stirred at 150° C. for 15 minutes under the irradiation with microwaves
  3. customThis reaction liquid
  4. additionwas diluted with a saturated aqueous common salt solution
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. additionacetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (8.5 μL, 0.072 mM) were added to the suspension
  9. stirringthe mixture was stirred at room temperature for one hour
  10. distillationThe solvent was distilled off from the reaction mixture
  11. customthe resulting residue was purified by the reversed phase HPLC

Sources & evidence

ORD record
ord-f6768de817bc40c9aa9c6d6ee21218a7
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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