Sodium hydride → HCID 58065516, compound

HRID 909555Notes

Reaction equation

HRID 909555 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:37])[C:10]([O:13][C:14]3[CH:15]=[C:16]([C:26]4[NH:30][C:29]([C:31]([NH:33][CH2:34][CH2:35]Cl)=[O:32])=[CH:28][CH:27]=4)[CH:17]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:19]=3)=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:37])[C:10]([O:13][C:14]3[CH:19]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:17]=[C:16]([C:26]4[NH:30][C:29]([C:31]5[O:32][CH2:35][CH2:34][N:33]=5)=[CH:28][CH:27]=4)[CH:15]=3)=[N:11][CH:12]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66681377HCID 66681377, compound

Product 1

HCID 58065516HCID 58065516, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(3-{[5-(Azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[(1S)-2-methoxy-1-methylethoxy]phenyl)-N-(2-chloroethyl)-1H-pyrrole-2-carboxamide (210 mg, 0.384 mmol) synthesized in Example (73a) was dissolved in tetrahydrofuran (10.0 mL), and sodium hydride (60%, 80 mg, 2.00 mmol) was added, followed by stirring at room temperature for 7.5 hours under nitrogen atmosphere. To the reaction solution, a saturated aqueous ammonium chloride solution (30 mL) was added, and extraction was carried out with dichloromethane (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) to afford the desired compound (120 mg, yield 62%) as a white 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)

Sources & evidence

ORD record
ord-f4eb1d95a13640d7baa6fa9d485f27b5
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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