tert-Butyl [3-(4-{[(1-adamantylmethyl)amino]carbonyl)-5-chloropyridin-2-yl)propyl](3-{[tert-butyl(dimethyl)silyl]oxy}propyl)carbamate → N-(1-Adamantylmethyl)-5-chloro-2-{3-[(3-hydroxypropyl)amino]propyl}isonicotinamide dihydrochloride

HRID 1247587Notes

Reaction equation

HRID 1247587 reaction equation
C(OC(=O)[N:7]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([C:28]([NH:30][CH2:31][C:32]23[CH2:41][CH:36]4[CH2:37][CH:38]([CH2:40][CH:34]([CH2:35]4)[CH2:33]2)[CH2:39]3)=[O:29])[C:25]([Cl:42])=[CH:24][N:23]=1)[CH2:8][CH2:9][CH2:10][O:11][Si](C(C)(C)C)(C)C)(C)(C)C>Cl.O1CCOCC1>[ClH:42].[ClH:42].[C:32]12([CH2:31][NH:30][C:28](=[O:29])[C:26]3[C:25]([Cl:42])=[CH:24][N:23]=[C:22]([CH2:21][CH2:20][CH2:19][NH:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:27]=3)[CH2:39][CH:38]3[CH2:40][CH:34]([CH2:35][CH:36]([CH2:37]3)[CH2:41]1)[CH2:33]2

Participants

4

Reactant 1

HCID 69586523tert-Butyl [3-(4-{[(1-adamantylmethyl)amino]carbonyl)-5-chloropyridin-2-yl)propyl](3-{[tert-butyl(dimethyl)silyl]oxy}propyl)carbamate

Product 1

HCID 21906713N-(1-Adamantylmethyl)-5-chloro-2-{3-[(3-hydroxypropyl)amino]propyl}isonicotinamide dihydrochlorideYield 201.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl[3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)propyl](3-{[tert-butyl(dimethyl)silyl]oxy}propyl)carbamate (Example 2(vi)) (0.46 g) was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and concentrated; the resultant solid was recrystallised from 1,4-dioxane/methanol and the solid collected by filtration to afford the titled compound (0.24 g) as a colourless powder.

Workup

  1. concentrationconcentrated
  2. customthe resultant solid was recrystallised from 1,4-dioxane/methanol
  3. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-d47d29fdca1f4226ad9216d21f72be99
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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