Hydrochloric Acid → 8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid N-isopropyl-hydrazide hydrochloride

HRID 708286Notes

Reaction equation

HRID 708286 reaction equation
C(OC([NH:8][N:9]([C:13]([C:15]1[S:16][C:17]2[CH2:18][CH2:19][O:20][C:21]3[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:22]=3[C:23]=2[N:24]=1)=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.[ClH:30].O1CCOCC1>CO>[ClH:30].[CH:10]([N:9]([C:13]([C:15]1[S:16][C:17]2[CH2:18][CH2:19][O:20][C:21]3[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:22]=3[C:23]=2[N:24]=1)=[O:14])[NH2:8])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58204215N'-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carbonyl)-N'-isopropyl-hydrazinecarboxylic acid tert-butyl ester

Product 1

HCID 670506528-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid N-isopropyl-hydrazide hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of N′-(8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carbonyl)-N′-isopropyl-hydrazinecarboxylic acid tert-butyl ester (6.14 g, 12.7 mmol) in methanol (49 mL) was treated with 4N HCl in dioxan (12.7 mL, 51.0 mmol) and stirred at RT for 0.75 h before being warmed to 50° C. and stirred for 3 h. The reaction mixture was concentrated in vacuo and the resultant solid was triturated with diethyl ether to give the title compound as a yellow brown solid (5.14 g, 12.3 mmol, 96%). LCMS: RT=4.79 min, [M+H]+=382/384.

Workup

  1. temperaturebefore being warmed to 50° C.
  2. stirringstirred for 3 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe resultant solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-065e8b5a602f4dfe8449872915c0a2b1
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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