Hydrazine → HCID 67515128, compound

HRID 2038776Notes

Reaction equation

HRID 2038776 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1([C:11]2O[C:13]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].BrN1C(=O)CCC1=O.[NH2:31][NH2:32]>C1COCC1.O>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1([C:11]2[N:31]=[N:32][C:13]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 67184N-bromobutanimideHCID 67516312HCID 67516312, compound

Product 1

HCID 67515128HCID 67515128, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

In a round bottom flask, {1-[5-(1-methyl-1H-pyrazol-4-yl)-furan-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester (226 mg, 0.745 mmol) was dissolved in a mixture of THF (12.4 mL) and water (1.3 mL). The flask was cooled to −35° C. in a dry ice/acetone bath (the mixture becomes a thick slurry) and then N-bromosuccinimide (146 mg, 0.819 mmol) was added as a solid in one portion. The reaction immediately turned a bright yellow color. The reaction was stirred for 15 min at this temperature after which time anhydrous hydrazine (0.21 mL, 6.7 mmol) was added in one portion via syringe. The ice bath was removed and the reaction was allowed to stir at room temperature for 20 h. The volatiles were removed at 50° C. under a stream of N2. The resulting residue was purified by flash chromatography (silica, 90→100% EtOAc/hexanes) to give 51 mg of {1-[6-(1-methyl-1H-pyrazol-4-yl)-pyridazin-3-yl]-cyclopropyl}-carbamic acid tert-butyl ester as a bright yellow solid, m/z 316.6 [M+H]+.

Workup

  1. additionwas added as a solid in one portion
  2. customThe reaction
  3. additionwas added in one portion via syringe
  4. customThe ice bath was removed
  5. customThe volatiles were removed at 50° C. under a stream of N2
  6. customThe resulting residue was purified by flash chromatography (silica, 90→100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c4eb693652334263babf7af8c569b4dc
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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