Hydrochloric Acid → HCID 59321103, compound

HRID 341163Notes

Reaction equation

HRID 341163 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][N:17]4[C:20]([C:23]5[CH:24]=[C:25]([CH:29]=[C:30]([N+:32]([O-])=O)[CH:31]=5)[C:26]([NH2:28])=[O:27])=[CH:21][N:22]=[C:16]4[CH:15]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>CCO.O.CO.[OH-].[OH-].[Pd+2]>[NH3:1].[CH3:3][OH:4].[NH2:32][C:30]1[CH:29]=[C:25]([CH:24]=[C:23]([C:20]2[N:17]3[CH:18]=[CH:19][C:14]([C:10]4[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[CH:9]=4)=[CH:15][C:16]3=[N:22][CH:21]=2)[CH:31]=1)[C:26]([NH2:28])=[O:27]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 59321053HCID 59321053, compound

Product 2

HCID 21705897Ammonia methanolHCID 59321103HCID 59321103, compoundYield 142.7%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of Pd(OH)2 (30 mg), 3-[7-(3-morpholin-4-ylmethyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-5-nitro-benzamide (135 mg), 2N HCl (0.15 ml) and HCO2NH4 (150 mg, 2.4 mmol) in EtOH/H2O (4:1, 5 ml) was stirred and heated at 90° C. under N2 for 90 minutes. After cooling to RT the mixture was diluted with MeOH and loaded on to a SCX cartridge. This was washed with MeOH, then 2M NH3-MeOH, to give the title compound (90 mg, gum). MS: [M+H]+ 428.

Workup

  1. temperatureAfter cooling to RT the mixture
  2. washThis was washed with MeOH

Sources & evidence

ORD record
ord-cd2064be96874202a23735ec481d82c5
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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