Ammonia → HCID 10160824, compound

HRID 1816070Notes

Reaction equation

HRID 1816070 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:13][C:14]2([NH:17]C(=O)OC(C)(C)C)[CH2:16][CH2:15]2)[CH2:10][CH2:11][OH:12])=[CH:4][C:3]=1[C:25]([NH:27][CH2:28][C:29]12[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2)=[O:26].Cl.N>CO.O1CCOCC1>[NH2:17][C:14]1([CH2:13][N:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH:4]=2)[C:25]([NH:27][CH2:28][C:29]23[CH2:30][CH:31]4[CH2:32][CH:33]([CH2:34][CH:35]([CH2:37]4)[CH2:36]2)[CH2:38]3)=[O:26])[CH2:10][CH2:11][OH:12])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86587155HCID 86587155, compound

Product 1

HCID 10160824HCID 10160824, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

[1-[[[[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-methyl](2-hydroxyethyl)amino]methyl]cyclopropyl]-carbamic acid, 1,1-dimethylethyl ester (Example 71d, 0.302 g) was dissolved in methanol (10 ml) and 4N HCl in dioxane (10 ml) was added. The mixture was stirred for 14 h at room temperature, 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 (eluting with 19:1:0.1 dichloromethane/methanol/ammonia) to afford the title compound as an oil (0.230 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give the free base
  3. customThis was purified by column chromatography over silica (eluting with 19:1:0.1 dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-299d850072704ab8ab4f084856af4949
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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