1,4-Dioxane hydrochloride → HCID 67338497, compound

HRID 1675885Notes

Reaction equation

HRID 1675885 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][C@H:39]([OH:43])[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][C:10]=1[F:44]>O1CCOCC1.C(Cl)Cl>[ClH:8].[ClH:1].[NH2:17][CH2:16][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[C:10]([F:44])[CH:11]=1)[C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[C:34]3[C@H:41]([CH3:42])[CH2:40][C@H:39]([OH:43])[C:35]=3[N:36]=[CH:37][N:38]=2)[CH2:29][CH2:28]1)=[O:26]

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86618949HCID 86618949, compound

Product 1

HCID 67338497HCID 67338497, compoundYield 179.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

4M HCl/dioxane (2.46 ml, 9.85 mmol) was added to a solution of tert-butyl (S)-2-(4-chloro-3-fluorophenyl)-3-(4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (0.263 g, 0.492 mmol) in dioxane (3 mL) and DCM (2 mL). The reaction mixture was stirred at room temperature for 13 hours and then concentrated to dryness. The residue was dissolved in minimal MeOH, and the solution was added dropwise to vigorously stirring ether (40 mL), which caused a fine precipitate to form. The solids were isolated by filtration through a medium frit funnel with nitrogen pressure, rinsed with ether, dried under nitrogen pressure, and dried further in vacuo to give (S)-3-amino-2-(4-chloro-3-fluorophenyl)-1-(4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride (0.224 g, 0.442 mmol, 89.7% yield) as a pale yellow powder. LC/MS (APCI+) m/z 434 [M+H]−.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in minimal MeOH
  3. additionthe solution was added dropwise to vigorously stirring ether (40 mL), which
  4. customto form
  5. customThe solids were isolated by filtration through a medium frit funnel with nitrogen pressure
  6. washrinsed with ether
  7. customdried under nitrogen pressure
  8. customdried further in vacuo

Sources & evidence

ORD record
ord-7fc7ee401c5d457784adbfb86bb69911
Source dataset
uspto-grants-2011_08
Patent number
US08003651B2

Reaction notes

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