Benzoyl isothiocyanate → HCID 178501176, compound

HRID 518596Notes

Reaction equation

HRID 518596 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1.[C:19]([N:27]=[C:28]=S)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[C:19](/[N:27]=[C:28]1/[N:8]([C@@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:14]2)[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[NH:1]/1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 178501200HCID 178501200, compound

Product 1

HCID 178501176HCID 178501176, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of cis-methyl 4-(3-aminopyridin-4-ylamino)cyclohexanecarboxylate (70 mg, 0.281 mmol) in ACN (5.6 mL) under nitrogen was added benzoyl isothiocyanate (0.045 mL, 0.337 mmol). The reaction mixture was stirred for 30 minutes at RT. To the mixture was added polymer-supported-carbodiimide (936 mg, 1.123 mmol; Loading: 1.2 mmol/g;), and the resulting mixture was stirred at 70° C. for 16 hours. The reaction mixture was cooled to RT and filtered, and the resin was washed with 1% MeOH/DCM. The filtrate was concentrated and purified by silica gel chromatography (1-4% MeOH/DCM) to afford cis-methyl 4-((E)-2-(benzoylimino)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylate as an off-white solid (18 mg, 17% yield). MS m/z=379.2 [M+H]. Calc'd for C21H22N4O3: 378.2.

Workup

  1. stirringthe resulting mixture was stirred at 70° C. for 16 hours
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered
  4. washthe resin was washed with 1% MeOH/DCM
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel chromatography (1-4% MeOH/DCM)

Sources & evidence

ORD record
ord-dec93dd54fa84194b26ae356a1a11dad
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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