Sodium hydride → HCID 58065432, compound

HRID 1964598Notes

Reaction equation

HRID 1964598 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14]2[N:15](C(OC(C)(C)C)=O)[C:16]([C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[CH:17][CH:18]=2)[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1.[N:31]1([C:35]([C:37]2[CH:38]=[C:39]([Cl:44])[C:40](Cl)=[N:41][CH:42]=2)=[O:36])[CH2:34][CH2:33][CH2:32]1.[H-].[Na+].[Cl-].[NH4+]>CS(C)=O>[N:31]1([C:35]([C:37]2[CH:38]=[C:39]([Cl:44])[C:40]([O:1][C:2]3[CH:3]=[C:4]([C:14]4[NH:15][C:16]([C:19]5[S:20][CH:21]=[CH:22][N:23]=5)=[CH:17][CH:18]=4)[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=3)=[N:41][CH:42]=2)=[O:36])[CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 536296165-(Azetidin-1-ylcarbonyl)-2,3-dichloropyridineHCID 66681373t-Butyl 2-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

Product 1

HCID 58065432HCID 58065432, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

t-Butyl 2-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate (70 mg, 0.163 mmol) synthesized in Example (38d) and 5-(azetidin-1-ylcarbonyl)-2,3-dichloropyridine (75 mg, 0.325 mmol) synthesized in Example (60a) were dissolved in dimethyl sulfoxide (5.0 mL), and sodium hydride (60%, 30 mg, 0.75 mmol) was added, and stirring was carried out at 100° C. for 3.5 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, a saturated aqueous ammonium chloride solution (30 mL) was added, and extraction was carried out with ethyl acetate (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=85%-100%) to afford the desired compound (58 mg, yield 68%) as a yellow solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=85%-100%)

Sources & evidence

ORD record
ord-f21d6e2a41984e68bc8caaaf88e86591
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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