Hydrochloric Acid → HCID 9851175, compound

HRID 411774Notes

Reaction equation

HRID 411774 reaction equation
C(O)(=O)C.[CH3:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[C:16](=[O:44])[N:17]([CH2:34][O:35][C:36]([CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[O:37])[C:18](=[O:33])[C:19]=2[C:20]2[C:28]3[C:23](=[CH:24][C:25]([N+:29]([O-:31])=[O:30])=[CH:26][CH:27]=3)[N:22]([CH3:32])[CH:21]=2)=[CH:7]1.C([O-])(O)=O.[Na+].[ClH:50]>C(OCC)(=O)C>[ClH:50].[CH3:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[C:16](=[O:44])[N:17]([CH2:34][O:35][C:36]([CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[O:37])[C:18](=[O:33])[C:19]=2[C:20]2[C:28]3[C:23](=[CH:24][C:25]([N+:29]([O-:31])=[O:30])=[CH:26][CH:27]=3)[N:22]([CH3:32])[CH:21]=2)=[CH:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 9851675HCID 9851675, compound

Product 1

HCID 9851175HCID 9851175, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Piperidine-4-carboxylic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester acetate salt, prepared as in example 9 above, was dissolved in ethyl acetate. The ethyl acetate solution was neutralized with cold saturated NaHCO3, was concentrated, and was taken up in 1:5 CH3CN:H2O. The resulting solution was treated with 2 equivalents of 2N aq. HCl and purified by HPLC to give the desired product (yield—86%).

Workup

  1. concentrationwas concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-165e880104f6404eb055f0e187fa6071
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Reaction notes

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