Ammonia → HCID 21900034, compound

HRID 719658Notes

Reaction equation

HRID 719658 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-0c92e91aebb74815a7f4f79a61e08c1a
Source dataset
uspto-grants-2006_11
Patent number
US07132457B2

Reaction notes

Loading…