Ethanol hydrochloride → HCID 67350105, compound

HRID 1672773Notes

Reaction equation

HRID 1672773 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]=[N: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]=[N: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 67349715HCID 67349715, compound

Product 1

HCID 67350105HCID 67350105, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-5-[5-(4-Tert-butoxycarbonylpiperazine-1-yl)pyridin-3-yl]-9-ethylamino-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (104 mg, 0.204 mmol) obtained in Step 1 was dissolved in ethanol (2 mL), and the mixture was stirred at room temperature for 1.5 hours after adding 4 mol/L hydrochloric acid-ethanol (3 mL). After concentrating the mixture, a saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (S)-9-ethylamino-5-[5-(piperazine-1-yl)pyridin-3-yl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (56.1 mg, 68%).

Workup

  1. concentrationAfter concentrating the mixture
  2. additiona saturated aqueous sodium bicarbonate solution was added
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b647a26722342029c72e8c9907390b5
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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