Ammonia → HCID 10160824, compound

HRID 1593838Notes

Reaction equation

HRID 1593838 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 4 N 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-952dc79a05aa4f35bc1f6b421873a24d
Source dataset
uspto-grants-2007_11
Patent number
US07297818B2

Reaction notes

Loading…