Ammonia → HCID 10135897, compound

HRID 719642Notes

Reaction equation

HRID 719642 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.N>O1CCOCC1.CO>[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 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86596764HCID 86596764, compound

Product 2

HCID 222AmmoniaHCID 10135897HCID 10135897, compoundYield 112%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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-3949a84703e64676ab97726280ece496
Source dataset
uspto-grants-2006_11
Patent number
US07132457B2

Reaction notes

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