Hydrochloric Acid → HCID 59835898, compound

HRID 1916766Notes

Reaction equation

HRID 1916766 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([O:28][CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[C:22]([CH:27]=3)[C:23]([O:25]C)=[O:24])=[N:14][CH:15]=2)=[CH:6][CH:5]=1.Cl>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([O:28][CH2:29][CH2:30][N:31]4[CH2:32][CH2:33][CH2:34][CH2:35]4)=[C:22]([CH:27]=3)[C:23]([OH:25])=[O:24])=[N:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10367021HCID 10367021, compound

Product 1

HCID 59835898HCID 59835898, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

1.6 mL aqueous 1 M NaOH are added to a solution of 369 mg (0.8 mmol) methyl 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzoate (Example 3.4) in 20 mL MeOH and the reaction mixture is heated to 70° C. for 3 h. It is combined with 1.6 mL 1 M HCl, evaporated down i.vac. and the residue is coevaporated twice with in each case 20 mL MeOH. The residue is triturated with EtOH with heating and suction filtered.

Workup

  1. customevaporated down i.vac
  2. customThe residue is triturated with EtOH
  3. temperaturewith heating
  4. filtrationsuction filtered

Sources & evidence

ORD record
ord-3da60334606d442da07ce92566246db1
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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