1,4-Dioxane hydrochloride → HCID 24786151, compound

HRID 82369Notes

Reaction equation

HRID 82369 reaction equation
[ClH:1].O1CCOCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:36]3[C:37]4[C@H:44]([CH3:45])[CH2:43][CH2:42][C:38]=4[N:39]=[CH:40][N:41]=3)[CH2:32][CH2:31]2)=[O:29])[CH2:16][N:17]([CH:25]([CH3:27])[CH3:26])C(=O)OC(C)(C)C)=[CH:11][CH:10]=1>O1CCOCC1>[ClH:8].[ClH:1].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([CH2:16][NH:17][CH:25]([CH3:27])[CH3:26])[C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:36]3[C:37]4[C@H:44]([CH3:45])[CH2:43][CH2:42][C:38]=4[N:39]=[CH:40][N:41]=3)[CH2:32][CH2:31]2)=[O:29])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67340744tert-butyl(S)-2-(4-chlorophenyl)-3-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate

Product 1

HCID 24786151HCID 24786151, compoundYield 189.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl/dioxane (7.83 ml, 31.3 mmol) was added to a slightly cloudy solution of tert-butyl(S)-2-(4-chlorophenyl)-3-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (0.679 g, 1.25 mmol) in dioxane (8 mL). The reaction mixture was stirred overnight under nitrogen (16 hours). The reaction mixture was concentrated to dryness and dried on a high vacuum line. The resulting residue was dissolved in minimal MeOH, and the solution was added dropwise to a stirring solution of ether, which caused a white precipitate to form. The resulting precipitate was isolated by filtration through a medium frit funnel with nitrogen pressure, rinsed with ether, dried with nitrogen pressure, dried in vacuo and then further in a 55° C. high vacuum oven for 2 days to give (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride (0.610 g, 94.6% yield) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customdried on a high vacuum line
  3. dissolutionThe resulting residue was dissolved in minimal MeOH
  4. additionthe solution was added dropwise to a stirring solution of ether, which
  5. customto form
  6. customThe resulting precipitate was isolated by filtration through a medium frit funnel with nitrogen pressure
  7. washrinsed with ether
  8. customdried with nitrogen pressure
  9. customdried in vacuo

Sources & evidence

ORD record
ord-db7d9e2bb2e24047906b77b2c3c1a4e0
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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