Hydrazine hydrate (1:1) → 3-Methyl-4-(pyrrolidin-1-yl)isothiazol-5-amine

HRID 1850701Notes

Reaction equation

HRID 1850701 reaction equation
O.NN.[CH3:4][C:5]1[C:9]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[C:8]([N:15]2C(=O)C3C(=CC=CC=3)C2=O)[S:7][N:6]=1>CCO>[CH3:4][C:5]1[C:9]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[C:8]([NH2:15])[S:7][N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 904110042-(3-Methyl-4-(pyrrolidin-1-yl)isothiazol-5-yl)isoindoline-1,3-dione

Product 1

HCID 904124253-Methyl-4-(pyrrolidin-1-yl)isothiazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (25.56 mg, 25.03 μL, 0.5106 mmol) was added to a solution of 2-(3-methyl-4-pyrrolidin-1-yl-isothiazol-5-yl)isoindoline-1,3-dione (160 mg, 0.5106 mmol) in EtOH (5 mL) and the mixture was stirred at RT for 10 min. The mixture was heated for 15 min at 120° C. in a microwave, then was concentrated in vacuo. The residue was purified by fractionlynx. The clean fractions were concentrated in vacuo and dried by azeotropic distillation with toluene (×2) to yield 3-methyl-4-(pyrrolidin-1-yl)isothiazol-5-amine as pale yellow solid. (61.7 mg, 59.9% over two steps). MS (ES+) 184.1.

Workup

  1. temperatureThe mixture was heated for 15 min at 120° C. in a microwave
  2. concentrationwas concentrated in vacuo
  3. customThe residue was purified by fractionlynx
  4. concentrationThe clean fractions were concentrated in vacuo
  5. dry with materialdried by azeotropic distillation with toluene (×2)

Sources & evidence

ORD record
ord-d44cf60d98f94626932eeed4c0ef5daf
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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