Hydrazine → HCID 67054482, compound

HRID 2406219Notes

Reaction equation

HRID 2406219 reaction equation
O=[C:2]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4][NH:3]1.F[B-](F)(F)F.[CH3:21][O+](C)C.[NH2:25][NH2:26]>ClCCl>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C:2]2[N:3]([CH:21]=[N:25][N:26]=2)[CH2:4][CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 226177365-Oxo-(1,4)diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 67054482HCID 67054482, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 5-oxo-1,4-diazepane-1-carboxylate (1000 mg, 4.67 mmol) in dichloromethane (10 mL) was added trimethyloxonium tetrafluoroborate (690 mg, 4.67 mmol) under nitrogen and the reaction mixture was stirred for 16 hours. At this point, formic hydrazine (280 mg, 4.67 mmol) in dichloromethane (8 mL) was added, and the reaction was stirred for an additional 16 hours. The reaction mixture was then concentrated under reduced pressure, resuspended in methanol (10 mL), and heated to reflux for 16 hours. The reaction mixture was concentrated and purified via flash chromatography on silica gel (0-50% 2N NH3 in methanol in CH2Cl2) to afford 4,5,7,8-tetrahydro-1,2,3a,6-tetraaza-azulene-6-carboxylic acid tert-butyl ester (680 mg, 61% yield). MS [m/z; (M+1)30 ]: 319.3

Workup

  1. stirringthe reaction was stirred for an additional 16 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. temperatureheated
  4. temperatureto reflux for 16 hours
  5. concentrationThe reaction mixture was concentrated
  6. custompurified via flash chromatography on silica gel (0-50% 2N NH3 in methanol in CH2Cl2)

Sources & evidence

ORD record
ord-c79aedefebe24857b60970ad4ebf1576
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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