Hydrazine hydrate (1:1) → HCID 21069852, compound

HRID 1788138Notes

Reaction equation

HRID 1788138 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[NH:5][NH:4]1.O.NN.FC(F)(F)C1(C2C=C(CN)C=CC=2)N=N1>C(O)C>[F:25][C:2]([F:1])([F:24])[C:3]1([C:6]2[CH:7]=[C:8]([CH2:9][NH2:10])[CH:21]=[CH:22][CH:23]=2)[NH:4][NH:5]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21069796HCID 21069796, compoundHCID 21069851HCID 21069851, compound

Product 1

HCID 21069852HCID 21069852, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of intermediate 65, 2-[3-(3-trifluoromethyl-diaziridin-3-yl)-benzyl]-isoindole-1,3-dione, (150 mg, 0.43 mmol) in ethanol (2 mL) was treated with hydrazine hydrate (0.4 mL) at room temperature and the solution stirred for 3.5 hrs. After removing ethanol in vacuo, the residue was partitioned between CH2Cl2 and water. The aqueous phase was acidified with dilute HCl, and washed with CH2Cl2. The aqueous phase was basified with dilute NaOH, and extracted with CH2Cl2. The organic extract was dried (MgSO4), filtered, and concentrated to obtain 50 mg (Yield 54%) of (3-(3-(trifluoromethyl)diaziridin-3-yl)phenyl)methanamine and (3-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanamine as a 1:1 mixture; 1H NMR (300 MHz, CDCl3) δ ppm: 3.85 (2 H, s) 3.88 (2 H, s) 7.08 (2 H, s) 7.31-7.40 (4 H, m) 7.43-7.50 (1 H, m, J=6.2 Hz) 7.54 (1 H, s); LC/MS m/z 216 (M+H for diazirine) and 218 (M+H for diaziridine).

Workup

  1. customAfter removing ethanol in vacuo
  2. customthe residue was partitioned between CH2Cl2 and water
  3. washwashed with CH2Cl2
  4. extractionextracted with CH2Cl2
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aaa5aabaae534c5d815aeb623e07bc90
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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