Ammonium Chloride → HCID 178507706, compound

HRID 707298Notes

Reaction equation

HRID 707298 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:14][C@H:13]([NH:15][C:16]2[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:12]1.[Cl-].[NH4+]>O.C(O)C.[Fe]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:12][C@H:13]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:14]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 178526676HCID 178526676, compound

Product 1

HCID 178507706HCID 178507706, compoundYield 69.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Trans-N1-(benzo[d]thiazol-2-yl)-N3-(3-nitropyridin-2-yl)cyclobutane-1,3-diamine (580 mg, 1.699 mmol), ammonium chloride (46 mg, 0.849 mmol) and iron dust (0.036 mL, 5.10 mmol) were suspended in a mixture of water (1.000 mL) and ethanol (3 mL). The reaction mixture was stirred at 50° C. for 16 hours then cooled and partitioned between water (100 mL) and ethyl acetate (100 mL). The organic phase was dried with sodium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to ethyl acetate gradient) gave N2-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)pyridine-2,3-diamine (370 mg, 1.188 mmol, 69.9% yield) as light-yellow solid.

Workup

  1. temperaturethen cooled
  2. custompartitioned between water (100 mL) and ethyl acetate (100 mL)
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-a3076b73b8364cfcb2c4bad5cf5c465e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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