Hydrochloric Acid → HCID 17984293, compound

HRID 1869234Notes

Reaction equation

HRID 1869234 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]Br)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH:36]([CH3:38])[CH3:37])[N:28]=2)=[O:26])[CH2:19][CH2:18]1.[ClH:39]>C(O)C.C(OCC)(=O)C>[ClH:39].[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25]([C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]([CH:36]([CH3:38])[CH3:37])[N:28]=3)=[O:26])[CH2:19][CH2:18]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 842214-(2-Bromoethyl)phenolHCID 21252890HCID 21252890, compound

Product 1

HCID 17984293HCID 17984293, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

2-(4-hydroxyphenyl)ethyl bromide (prepared as described in Acta Chem. Scand. 21 (1) 53-62, 1967) (3.4 g, 0.017 moles) and anhydrous potassium carbonate (4.6 g, 0.033 moles) in absolute ethanol (100 ml) were added to a solution of N-(4-piperidinylmethyl)-1-isopropyl-1H-3 indazolecarboxamide (4.2 g, 0.014 moles), prepared as described in EP-A-0 975 623 in absolute ethanol (80 ml). The suspension thus obtained was stirred continuously under reflux for 16 hours. The suspension was filtered and the filtrate evaporated under reduced pressure. The residue thus obtained was then transformed into the corresponding hydrochloride salt by dissolution in ethyl acetate, addition of ethanolic hydrogen chloride and recrystallisation from absolute ethanol to give the desired product (2.2 g).

Workup

  1. customprepared
  2. customThe suspension thus obtained
  3. temperatureunder reflux for 16 hours
  4. filtrationThe suspension was filtered
  5. customthe filtrate evaporated under reduced pressure
  6. customThe residue thus obtained

Sources & evidence

ORD record
ord-1a8a0cc5e4e64dd5b2692b6f3ba5d969
Source dataset
uspto-grants-2009_12
Patent number
US07638534B2

Reaction notes

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