1,4-Dioxane hydrochloride → HCID 67540515, compound

HRID 1192343Notes

Reaction equation

HRID 1192343 reaction equation
C([C@@:8]([NH2:34])([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[CH:25]=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:10])(OC(C)(C)C)=O.[ClH:35].O1CCOCC1>O1CCOCC1>[ClH:33].[ClH:35].[NH2:34][C@H:8]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[CH:25]=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:10]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67540643HCID 67540643, compound

Product 1

HCID 67540515HCID 67540515, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2R)-2-Boc-amino-3-(4-chlorophenyl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one in 1 mL dioxane was added 1 mL 4M HCl/dioxane. The resulting suspension was stirred at room temperature overnight, after which it was concentrated to dryness. The solids were dissolved in minimal MeOH and then triturated with ether. The resulting solids were isolated by filtration through a flitted funnel with nitrogen pressure, rinsed with ether, and dried in vacuo to give (2R)-2-amino-3-(4-chlorophenyl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one dihydrochloride (19 mg, 38%) as a pink powder. 1H NMR (D2O, 400 MHz) δ 8.16 (1H, s), 7.27 (1H, s), 7.18-7.11 (4H, m), 6.68 (1H, s), 4.60-4.56 (1H, m), 3.98-3.69 (4H, m), 3.61-3.52 (2H, m), 3.45-3.37 (1H, m), 3.20-3.12 (1H, m), 3.00-2.91 (2H, m). LCMS (APCI+) m/z 385 [M+H]+. HPLC Rt 1.68 min.

Workup

  1. concentrationafter which it was concentrated to dryness
  2. dissolutionThe solids were dissolved in minimal MeOH
  3. customtriturated with ether
  4. customThe resulting solids were isolated by filtration through a flitted funnel with nitrogen pressure
  5. washrinsed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2c30f77a05454d3ba26052a651c5f6bc
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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