Benzoate → HCID 178437863, compound

HRID 619186Notes

Reaction equation

HRID 619186 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 reluxed 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 cooled
  4. customthe product was isolated by filtration
  5. customdried at 90° C.

Sources & evidence

ORD record
ord-bf43da5f84fd404cb2e2b84fbcb685ef
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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