Methanol → HCID 136364591, compound

HRID 2073627Notes

Reaction equation

HRID 2073627 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=3[F:19])[C:10]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[C:9]([CH2:26][O:27][CH2:28][CH2:29][N:30]3C(=O)C4=CC=CC=C4C3=O)[NH:8][C:7]=12)#[N:2].CO.O.NN.C(Cl)(Cl)[Cl:47]>>[ClH:47].[NH2:30][CH2:29][CH2:28][O:27][CH2:26][C:9]1[NH:8][C:7]2[N:6]([N:5]=[CH:4][C:3]=2[C:1]#[N:2])[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[C:10]=1[C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 24654Hydrazine hydrate (1:1)HCID 136364592HCID 136364592, compound

Product 1

HCID 136364591HCID 136364591, compound

Conditions

Temperature
50 °C

Procedure

To a solution of 1.3 g of isopropyl 3-cyano-7-(2,3-difluorophenyl)-5-[2-(phthalimido)ethoxymethyl]-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate in a mixed solvent of 12 ml of methanol and 12 ml of chloroform is added 142 μl of hydrazine hydrate and the mixture is refluxed at 50° C. for 5 hours. After the solvent is distilled off, to the residue is added aqueous sodium hydrogencarbonate and then extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulfate and ethanolic hydrochloric acid is added to convert into hydrochloride. The obtained crystals are recrystallized from methanol to give 0.4 g of isopropyl 5-(2-aminoethoxymethyl)-3-cyano-7-(2,3-difluorophenyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate hydrochloride 1/4 hydrate.

Workup

  1. distillationAfter the solvent is distilled off, to the residue
  2. additionis added aqueous sodium hydrogencarbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialdried over sodium sulfate and ethanolic hydrochloric acid
  6. additionis added
  7. customThe obtained crystals are recrystallized from methanol

Sources & evidence

ORD record
ord-a0ec6ba8946e4a8888c856c1fd9ec0c4
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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