1-Isopropylhydrazine hydrochloride → 8-Bromo-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1190727Notes

Reaction equation

HRID 1190727 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]=[C:8]([C:14]([NH2:16])=O)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.CO[C:21](OC)(N(C)C)[CH3:22].Cl.[CH:29]([NH:32][NH2:33])([CH3:31])[CH3:30]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[N:32]([CH:29]([CH3:31])[CH3:30])[N:33]=[C:21]([CH3:22])[N:16]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 855731-Isopropylhydrazine hydrochlorideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 670505308-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

Product 1

HCID 582039088-Bromo-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (9.040 g, 0.02780 mol) in Toluene (150 mL) was added dimethylacetamide-dimethylacetal (12.38 mL, 0.08340 mol). The reaction was stirred at 95° C. for 4 hours. The toluene was then removed in vacuo and the crude was carried forward without further purification. The crude material was redissolved in acetic acid (90 mL). Isopropylhydrazine hydrochloride (3.689 g, 0.03336 mol) was added and the reaction was stirred at room temperature overnight. The acetic acid was then removed in vacuo. The crude material was triturated in isopropyl alcohol, and filtered to give 8-Bromo-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene as a light yellow solid (10.422 g). MS (ESI+) 405.0/407.0

Workup

  1. customThe toluene was then removed in vacuo
  2. customthe crude was carried forward without further purification
  3. dissolutionThe crude material was redissolved in acetic acid (90 mL)
  4. stirringthe reaction was stirred at room temperature overnight
  5. customThe acetic acid was then removed in vacuo
  6. customThe crude material was triturated in isopropyl alcohol
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ddae79c752904c2c98c1e6294a2f619b
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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