Sodium hydride → HCID 86757585, compound

HRID 429059Notes

Reaction equation

HRID 429059 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH3:38])[CH2:15][CH2:16][NH:17][C:18]([C:20]3([NH:30][C:31]([O:33]C(C)(C)C)=O)[C:28]4[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)=[O:19])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+]>O1CCCC1.C(OCC)(=O)C>[ClH:29].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([CH:14]([CH3:38])[CH2:15][CH2:16][N:17]3[C:18](=[O:19])[C:20]4([C:28]5[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[NH:30][C:31]3=[O:33])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 86757586HCID 86757586, compound

Product 1

HCID 86757585HCID 86757585, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (+/−)N-{3-[4-(4-fluorophenyl)piperidin-1-yl]butyl}-1-tert-butoxycarbonylamino-5-chloro-indane-1-carboxamide (170 mg, 0.31 mmol) in tetrahydrofuran (4 mL) was added 60% sodium hydride/mineral oil (30 mg, 0.7 mmol) and the reaction mixture was warmed at 50° C. for one hour. The cooled reaction was diluted with ethyl acetate, washed with aqueous sat'd sodium bicarbonate, dried (anhyd. sodium sulfate), filtered, and the solvent concentrated under vacuum. The residue was triturated with methanol and the solid product collected by filtration. This material was suspended in methanol (3 mL) and 1 HCl/diethyl ether (0.25 mL) was added. Upon dilution with more diethyl ether the product salt slowly precipitated and solidified to give the title compound. By chiral HPLC this is a mixture of at least three diastereomers.

Workup

  1. customThe cooled reaction
  2. washwashed with aqueous sat'd sodium bicarbonate
  3. dry with materialdried (anhyd. sodium sulfate)
  4. filtrationfiltered
  5. concentrationthe solvent concentrated under vacuum
  6. customThe residue was triturated with methanol
  7. filtrationthe solid product collected by filtration
  8. addition1 HCl/diethyl ether (0.25 mL) was added
  9. customUpon dilution with more diethyl ether the product salt slowly precipitated

Sources & evidence

ORD record
ord-a4391cd7c3404e63afad4d4a8132767b
Source dataset
uspto-grants-2001_11
Patent number
US06316437B1

Reaction notes

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