Ammonia → HCID 10135897, compound

HRID 1816056Notes

Reaction equation

HRID 1816056 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][CH2:11][CH2:12][N:13](C)[C:14](=O)OC(C)(C)C)=[CH:4][C:3]=1[C:22]([NH:24][CH2:25][C:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2)=[O:23].Cl.CO.N>O1CCOCC1>[NH3:13].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][CH2:11][CH2:12][NH:13][CH3:14])=[CH:4][C:3]=1[C:22]([NH:24][CH2:25][C:26]12[CH2:33][CH:32]3[CH2:31][CH:30]([CH2:29][CH:28]([CH2:34]3)[CH2:27]1)[CH2:35]2)=[O:23]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 887MethanolHCID 86596764HCID 86596764, compound

Product 2

HCID 222AmmoniaHCID 10135897HCID 10135897, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[3-[[4-Chloro-3-[[(tricyclo[3.3. 1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-methoxy]propyl]methyl-carbamic acid, 1,1-dimethylethyl ester (0.236 g, Example 23b), 4M hydrogen chloride in 1,4-dioxane (5 ml and methanol (5 ml) were stirred together under nitrogen for 3 h, then poured into 25% aqueous ammonia solution and concentrated under reduced pressure to give the free base. This was purified by column chromatography over silica gel, eluting with 19:1:0.1/dichloromethane:methanol: ammonia to afford the title compound as an oil (0.106 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give the free base
  3. customThis was purified by column chromatography over silica gel
  4. washeluting with 19:1:0.1/dichloromethane

Sources & evidence

ORD record
ord-c5cf65b82923457098aa41212d99f113
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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