Cyclopentylamine → HCID 22741967, compound

HRID 49895Notes

Reaction equation

HRID 49895 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])O.[Na+]>ClCCl>[CH:19]1([NH:24][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 516892Sodium BicarbonateHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 22741967HCID 22741967, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 0.3 g (1.173 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.4 g (4.692 mmol) cyclopentylamine is stirred for 6 h at 115° C. The cooled reaction mixture is then distributed between dichloromethane and saturated aqueous sodium hydrogencarbonate solution. The organic solution washed with brine and dried over anhydrous sodium sulfate is evaporated and the residue purified on silica gel by flash chromatography using acetate/methanol (9:1). Title compound is obtained after crystallization of the product-containing fractions from acetonitrile/water and drying under HV (8 h, 100° C.); m.p. 163-165° C.; ESI-MS: (M+H)+=305.

Workup

  1. customThe cooled reaction mixture
  2. washThe organic solution washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customis evaporated
  5. customthe residue purified on silica gel by flash chromatography

Sources & evidence

ORD record
ord-341da6b698e7474fbf81c9387c641f13
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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