Water → HCID 58204481, compound

HRID 1629073Notes

Reaction equation

HRID 1629073 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7]/[C:8](=[N:11]\[C:12]([C:14]1[N:23]=[C:22]2[N:16]([CH2:17][CH2:18][O:19][C:20]3[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:21]=32)[CH:15]=1)=O)/SC)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl.[CH:40]([NH:43][NH2:44])([CH3:42])[CH3:41].O>CN(C)C=O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[N:11]=[C:12]([C:14]2[N:23]=[C:22]3[N:16]([CH2:17][CH2:18][O:19][C:20]4[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:21]=43)[CH:15]=2)[N:43]([CH:40]([CH3:42])[CH3:41])[N:44]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 178503946HCID 178503946, compound

Product 1

HCID 58204481HCID 58204481, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {[(E)-8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carbonylimino]-methylthiomethyl}-carbamic acid tert-butyl ester (0.658 g, 0.00137 mol) in N,N-dimethylformamide (7.50 mL) was added N,N-Diisopropylethylamine (0.9524 mL, 0.005468 mol) then isopropylhydrazine hydrochloride (0.2267 g, 0.002050 mol). The reaction was stirred at room temperature for 4 h. Water and methylene chloride were added and the mixture was extracted 3× with methylene chloride. The organic layers were combined, dried with MgSO4 and concentrated. The crude was purified by flash chromatography (0-10% MeOH in DCM) to give [5-(8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-2-yl)-1-isopropyl-1H-[1,2,4]triazol-3-yl]-carbamic acid tert-butyl ester (642 mg) a sticky light yellow solid. The material was carried forward without any further purification. MS(ESI+) 489.1/491.1

Workup

  1. extractionthe mixture was extracted 3× with methylene chloride
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. customThe crude was purified by flash chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-0497d33ec4a14eccba5b43fe001b733b
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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