Benzoate → HCID 178437863, compound

HRID 1597880Notes

Reaction equation

HRID 1597880 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:24]=[C:25]([O:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:26]=2)[C:13](OCCN2CCOCC2)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:36]1([N:41]2[C:45]([NH2:46])=[C:44]([C:47]([NH2:49])=[O:48])[C:43]([CH2:50][CH3:51])=[N:42]2)[CH2:40][CH2:39][CH2:38][CH2:37]1.O(C)[Na].C([O-])(=O)C1C=CC=CC=1>C(O)(=O)C.O.C(O)C>[CH:36]1([N:41]2[C:45]3=[N:46][C:13]([C:12]4[CH:11]=[C:10]([O:9][CH2:8][CH2:7][N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)[CH:26]=[C:25]([O:27][CH2:28][CH2:29][N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)[CH:24]=4)=[N:49][C:47](=[O:48])[C:44]3=[C:43]([CH2:50][CH3:51])[NH:42]2)[CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

8

Reactant 4

HCID 242BenzoateHCID 21846072HCID 21846072, compoundHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamideHCID 178418582HCID 178418582, compound2×

Product 1

HCID 178437863HCID 178437863, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-morpholinylethyl 3,5-di-[2-(4-morpholinyl)ethoxy]benzoate (2.0 g, 4 mmol), 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (0.45 g, 2 mmol), NaOCH3 (0.23 g, 4 mmol) and ethanol (50 ml) was refluxed for 96 hours. The reaction was incomplete so an additional equivalent of the benzoate and NaOCH3 were added and the mixture was refluxed for 48 hours. The reaction mixture was stripped to dryness, and the residue was treated with water and acidified with acetic acid. The mixture was cooled and the product was isolated by filtration and dried at 90° C. to afford 0.61 g (54%) of 1-cyclopentyl-3-ethyl-6-[3,5-di[2-(4-morpholinyl)ethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 182°-183° C.

Workup

  1. temperaturewas refluxed for 96 hours
  2. additionwere added
  3. temperaturethe mixture was refluxed for 48 hours
  4. temperatureThe mixture was cooled
  5. customthe product was isolated by filtration
  6. customdried at 90° C.

Sources & evidence

ORD record
ord-b7564e4999504d2eab89ecd7d20ccde7
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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