Dimethyl Sulfoxide → HCID 15952466, compound

HRID 2244267Notes

Reaction equation

HRID 2244267 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([I:26])=[C:22]([CH3:27])[CH:21]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].CS(C)=O.[NH2:35][CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1>C(#N)C>[I:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:35][CH2:36][C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:28])=[CH:21][C:22]=1[CH3:27]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 310183-PyridinemethanamineHCID 68688004HCID 68688004, compound

Product 1

HCID 15952466HCID 15952466, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,2,2-trichloro-1-[10-(4-iodo-3-methylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]ethanone of Step B (1 g, 1.74 mmol) in dry acetonitrile (30 mL) at room temperature under nitrogen was added dimethyl sulfoxide (0.62 mL, 8.72 mmol) followed by 3-(aminomethyl)pyridine (0.36 mL, 3.49 mmol) and the reaction mixture heated to reflux for 36 hours. The cooled reaction mixture was concentrated in vacuo to a small volume then partitioned between ethyl acetate (50 mL) and 1 M sodium hydroxide (50 mL). The organic layer was separated, washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a yellow foam. Purification by flash chromatography using ethyl acetate as solvent afforded a white foam (0.94 g). Recrystallization from ethyl acetate/hexane gave the title compound (0.77 g, 79%) as white solid, m.p. 176-177° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 36 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated in vacuo to a small volume
  5. customthen partitioned between ethyl acetate (50 mL) and 1 M sodium hydroxide (50 mL)
  6. customThe organic layer was separated
  7. washwashed with water (50 mL) and brine (50 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford a yellow foam
  11. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d9165d24eeb44fd6ad8266acb504f8d9
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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