1,4-Dioxane hydrochloride → 3-Oxo-4-[2-((2R,5S)-5-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}piperidin-2-yl)ethyl]-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

HRID 255347Notes

Reaction equation

HRID 255347 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][C@H:15]3[CH2:20][CH2:19][C@H:18]([NH:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]5[O:27][CH2:28][C:29](=[O:33])[NH:30][C:31]=5[N:32]=4)[CH2:17][N:16]3C(OC(C)(C)C)=O)[C:7]=2[CH:41]=1)#[N:2].Cl.O1CCOCC1>O1CCOCC1>[O:12]=[C:9]1[N:8]([CH2:13][CH2:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([NH:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]4[O:27][CH2:28][C:29](=[O:33])[NH:30][C:31]=4[N:32]=3)[CH2:17][NH:16]2)[C:7]2[CH:41]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66774765tert-butyl (2R,5S)-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-5-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}piperidine-1-carboxylate2×

Product 1

HCID 667749633-Oxo-4-[2-((2R,5S)-5-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}piperidin-2-yl)ethyl]-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrileYield 64.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (2R,5S)-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-5-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}piperidine-1-carboxylate (Intermediate 182, 0.138 g) in dioxane (2 mL) was added 4M HCl/dioxane (1 mL). After 1 hour at room temperature, the reaction was concentrated and evaporated twice from methanol. The solid was suspended in methanol and filtered to yield 73 mg of the name compound as a bis HCl salt.

Workup

  1. concentrationthe reaction was concentrated
  2. customevaporated twice from methanol
  3. filtrationfiltered

Sources & evidence

ORD record
ord-727c073f16d14c80a02bd84aa7a56960
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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