Ammonia → HCID 21900034, compound

HRID 1816072Notes

Reaction equation

HRID 1816072 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([C:24]([NH:26][CH2:27][C:28]23[CH2:37][CH:32]4[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]4)[CH2:29]2)[CH2:35]3)=[O:25])[CH:18]=1)[CH2:5][CH2:6][N:7](C)[C:8](=O)OC(C)(C)C.Cl.N>CO.O1CCOCC1>[OH:1][CH2:2][CH2:3][N:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH:18]=1)[C:24]([NH:26][CH2:27][C:28]12[CH2:29][CH:30]3[CH2:36][CH:34]([CH2:33][CH:32]([CH2:31]3)[CH2:37]1)[CH2:35]2)=[O:25])[CH2:5][CH2:6][NH:7][CH3:8]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86596766HCID 86596766, compound

Product 1

HCID 21900034HCID 21900034, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

[2-[(2-Hydroxyethyl)[[4-methyl-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]methyl]amino]ethyl]methyl-carbamic acid, 1,1-dimethylethyl ester (Example 72a, 0.285 g) was dissolved in methanol (10 ml), 4N HCl in dioxane (10 ml) was added and the mixture stirred for 14 h at room temperature. The solution was poured into 25% aqueous ammonia solution and concentrated under reduced pressure to give the free base. This was purified by chromatography over silica gel (eluting with 8:2:0.2/dichloromethane:methanol: ammonia) to afford the title compound as an oil (0.167 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give the free base
  3. customThis was purified by chromatography over silica gel (eluting with 8:2:0.2/dichloromethane:methanol: ammonia)

Sources & evidence

ORD record
ord-4e4c3fc2ac9e4e6ab7bcfdb208eb4b03
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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