1,4-Dioxane hydrochloride → HCID 67339957, compound

HRID 82385Notes

Reaction equation

HRID 82385 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[CH: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][C:17]([NH:20]C(=O)OC(C)(C)C)([CH3:19])[CH3:18])=[CH:11][CH:10]=1>O1CCOCC1>[ClH:8].[ClH:1].[NH2:20][C:17]([CH3:18])([CH3:19])[CH2:16][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=1)[C:28]([N:30]1[CH2:31][CH2:32][N:33]([C:36]2[C:37]3[CH:44]([CH3:45])[CH2:43][CH2:42][C:38]=3[N:39]=[CH:40][N:41]=2)[CH2:34][CH2:35]1)=[O:29]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67341311(R)-tert-butyl 4-(4-chlorophenyl)-2-methyl-5-(4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-5-oxopentan-2-ylcarbamate

Product 1

HCID 67339957HCID 67339957, compoundYield 167.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl/dioxane (0.609 ml, 2.43 mmol) was added to a solution of (R)-tert-butyl 4-(4-chlorophenyl)-2-methyl-5-(4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-5-oxopentan-2-ylcarbamate (0.044 g, 0.0812 mmol) in dioxane (1 mL). The reaction mixture was stirred at room temperature for 2 days, after which it was concentrated to dryness. The resulting residue dissolved in minimal MeOH, and the product was triturated by the addition of ether. The solids were isolated by filtration through quantitative membrane filter paper with nitrogen pressure, rinsed with ether, and dried in vacuo to give (R)-4-amino-2-(4-chlorophenyl)-4-methyl-1-(4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)pentan-1-one dihydrochloride (0.035 g, 83.7% yield) as a white powder. LC/MS (APCI+) m/z 442 [M+H]+. 1:1 mixture of diastereomers.

Workup

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

Sources & evidence

ORD record
ord-418691b96c654342b81a764d5c99d046
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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