Ethanol hydrochloride → HCID 67348346, compound

HRID 1672845Notes

Reaction equation

HRID 1672845 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([N:20]3[CH2:29][C@H:28]4[N:24]([CH2:25][CH2:26][CH2:27]4)[C:23]4[N:30]=[C:31]([NH:34][CH2:35][CH3:36])[N:32]=[CH:33][C:22]=4[C:21]3=[O:37])[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(O)C>C(O)C>[CH2:35]([NH:34][C:31]1[N:32]=[CH:33][C:22]2[C:21](=[O:37])[N:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:15]=3)[CH2:29][C@H:28]3[N:24]([CH2:25][CH2:26][CH2:27]3)[C:23]=2[N:30]=1)[CH3:36]

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 67352368HCID 67352368, compound

Product 1

HCID 67348346HCID 67348346, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-5-[3-(4-Tert-butoxycarbonylpiperazine-1-yl)phenyl]-9-ethylamino-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (0.235 g, 0.643 mmol) obtained in Step 3 was dissolved in ethanol (3 mL), and the mixture was stirred at room temperature for 1 hour after adding 4 mol/L hydrochloric acid-ethanol (3 mL). The mixture was concentrated, and extracted with chloroform after adding a saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the residue obtained by concentrating the organic layer was purified by silica gel column chromatography to give (S)-9-ethylamino-5-[3-(piperazine-1-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (0.185 g, quantitative).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with chloroform
  3. additionafter adding a saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe residue obtained
  6. concentrationby concentrating the organic layer
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-000aa9958eda49abab0027988c5eaaab
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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