Sodium hydride → HCID 58065534, compound

HRID 909549Notes

Reaction equation

HRID 909549 reaction equation
[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:13]=[C:14]([C:24]4[NH:28][C:27]([C:29]([NH:31][CH2:32][CH2:33]Cl)=[O:30])=[CH:26][CH:25]=4)[CH:15]=[C:16]([O:18][C@@H:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=3)=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:13]=[C:14]([C:24]4[NH:28][C:27]([C:29]5[O:30][CH2:33][CH2:32][N:31]=5)=[CH:26][CH:25]=4)[CH:15]=[C:16]([O:18][C@@H:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=3)=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66681427HCID 66681427, compound

Product 1

HCID 58065534HCID 58065534, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-{3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-N-(2-chloroethyl)-1H-pyrrole-2-carboxamide (85 mg, 0.16 mmol) synthesized in Example (68a) was dissolved in tetrahydrofuran (3 mL), and sodium hydride (37 mg, 0.82 mmol) was added at 0° C., followed by stirring at room temperature for 20 hours. To the reaction solution, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out with ethyl acetate (50 mL). After washing with saturated brine, drying was carried out 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 100%-methanol/chloroform=2%) to afford the desired product (33 mg, yield 41%) as a pale yellow solid.

Workup

  1. extractionextraction
  2. washAfter washing with saturated brine
  3. customdrying
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate 100%-methanol/chloroform=2%)

Sources & evidence

ORD record
ord-e13e3c920b584c43810a45847862c607
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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