HCID 11504490, compound → HCID 57736689, compound

HRID 2080345Notes

Reaction equation

HRID 2080345 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH3:21])[CH2:16]3)[CH:9]=2)=[CH:6][C:5]([CH2:22][NH:23][C:24](=O)[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH:26]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH3:21])[CH2:16]3)[CH:9]=2)=[CH:6][C:5]([CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH:26]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11504490HCID 11504490, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57736689HCID 57736689, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of N-[(6-fluoro-3′-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-3-(4-piperidinylmethyl)benzamide (100 mg, 0.194 mmol) in THF (2.0 mL) was added to lithium aluminum hydride (1.0 N in THF, 2 mL, 2 mmol). The mixture was heated in a microwave reactor at 80° C. for 60 minutes. After cooling to room temperature, the reaction mixture was carefully quenched with saturated Na2SO4, filtered through celite, dried over K2CO3 and concentrated under vacuum to give a crude oil. Further purification by Gilson reverse phase HPLC, eluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min), gave the title compound (80 mg, 82%) as an oil. LC/MS: m/z, 502 (M+H), 1.29 min.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was carefully quenched with saturated Na2SO4
  3. filtrationfiltered through celite
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated under vacuum
  6. customto give a crude oil
  7. customFurther purification by Gilson reverse phase HPLC
  8. washeluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min)

Sources & evidence

ORD record
ord-38cc27f74241456f8f9831e775ef98a6
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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