Methanesulfonic Acid → HCID 178437843, compound

HRID 1597890Notes

Reaction equation

HRID 1597890 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=O)[CH2:3]1.[CH:18]1([N:23]2[C:27]([NH2:28])=[C:26]([C:29]([NH2:31])=[O:30])[C:25]([CH2:32][CH3:33])=[N:24]2)[CH2:22][CH2:21][CH2:20][CH2:19]1.CS(O)(=O)=O>C(Cl)Cl>[CH:18]1([N:23]2[C:27]3=[N:28][C:13]([C:12]4[CH:15]=[CH:16][CH:17]=[C:10]([O:9][CH:4]5[CH2:5][CH2:6][CH2:7][CH2:8][N:2]([CH3:1])[CH2:3]5)[CH:11]=4)=[N:31][C:29](=[O:30])[C:26]3=[C:25]([CH2:32][CH3:33])[NH:24]2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 21846078HCID 21846078, compoundHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437843HCID 178437843, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(1-methyl-3-hexahydroazepinyloxy) benzaldehyde (0.79 g, 3.4 mol), 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (0.5 g, 2.2 mmol), methanesulfonic acid (0.25 ml) and xylenes (25 ml) was refluxed overnight. The solvent was stripped, the residue was dissolved in CH2Cl2 and purified by column chromatography on silica gel eluting with ether, then acetone, then 0.5% Et3N/acetone to afford 0.43 g (45%) of 1-cyclopentyl-3-ethyl-6-[3-(1-methyl-3-hexahydroazepinyloxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 195°-196° C.

Workup

  1. temperaturewas refluxed overnight
  2. custompurified by column chromatography on silica gel eluting with ether

Sources & evidence

ORD record
ord-8505dcd3f16e4cf1b789171924a2013f
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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