1,4-Dioxane hydrochloride → HCID 67339956, compound

HRID 82390Notes

Reaction equation

HRID 82390 reaction equation
[ClH:1].O1CCOCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([C:25]([N:27]2[CH2:32][CH2:31][N:30]([C:33]3[C:34]4[C@H:41]([CH3:42])[CH2:40][CH2:39][C:35]=4[N:36]=[CH:37][N:38]=3)[CH2:29][CH2:28]2)=[O:26])[CH2:16][NH:17]C(=O)OC(C)(C)C)=[CH:11][CH:10]=1>O1CCOCC1>[ClH:8].[ClH:1].[NH2:17][CH2:16][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=1)[C:25]([N:27]1[CH2:28][CH2:29][N:30]([C:33]2[C:34]3[C@H:41]([CH3:42])[CH2:40][CH2:39][C:35]=3[N:36]=[CH:37][N:38]=2)[CH2:31][CH2:32]1)=[O:26]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86618948tert-butyl (S)-2-(4-chlorophenyl)-3-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate

Product 1

HCID 67339956HCID 67339956, compoundYield 157.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl/dioxane (0.860 ml, 3.44 mmol) was added to a 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-oxopropylcarbamate (0.043 g, 0.0860 mmol) in dioxane (1.2 mL). The reaction mixture was stirred at room temperature overnight (16 hours), after which it was concentrated and dried on high vacuum line. The resulting residue was dissolved in minimal MeOH, and the product was triturated by the addition of ether. The resulting solids were isolated by filtration through Varian quantitative membrane filter paper with nitrogen pressure, rinsed with ether, dried with nitrogen pressure, and further dried in vacuo to give (S)-3-amino-2-(4-chlorophenyl)-1-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride (0.032 g, 78.7% yield) as a white powder. LC/MS (APCI+) m/z 400 [M+H]+.

Workup

  1. concentrationafter which it was concentrated
  2. customdried on high vacuum line
  3. dissolutionThe resulting residue was dissolved in minimal MeOH
  4. customthe product was triturated by the addition of ether
  5. customThe resulting solids were isolated by filtration through Varian quantitative membrane
  6. filtrationfilter paper with nitrogen pressure
  7. washrinsed with ether
  8. customdried with nitrogen pressure
  9. customfurther dried in vacuo

Sources & evidence

ORD record
ord-bdd42226ae12433abf0c4db17e146b67
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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