Hydrazine hydrate (1:1) → HCID 178514315, compound

HRID 1509312Notes

Reaction equation

HRID 1509312 reaction equation
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=S)[CH2:8][O:7][C:6]=2[N:12]=1.O.[NH2:20][NH2:21]>O1CCCC1>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10]/[C:9](=[N:20]/[NH2:21])/[CH2:8][O:7][C:6]=2[N:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866836666-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione

Product 1

HCID 178514315HCID 178514315, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 15 ml vial was 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione (100 mg, 0.311 mmol) and hydrazine monohydrate (0.049 ml, 1.557 mmol) in tetrahydrofuran (5 ml) to give a brown solution. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and the crude residue was slurred in diethyl ether. The supernatant solvent was removed and the brown solid vas dried until constant weigh to afford the title compound (90 mg, 90%). It was used for the next step without further purification. LCMS (Method D): RT 0.770 min, M+1=321.

Workup

  1. customto give a brown solution
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe supernatant solvent was removed
  4. customthe brown solid vas dried

Sources & evidence

ORD record
ord-a954f6df6d8246caa17f62ca84978fe0
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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