Water → HCID 10002649, compound

HRID 1787488Notes

Reaction equation

HRID 1787488 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:33]=[CH:32][C:13]3[N:14]([C:17]4[N:22]=[C:21]([NH:23][C@H:24]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH3:25])[CH:20]=[N:19][CH:18]=4)[CH:15]=[N:16][C:12]=3[CH:11]=2)=O)[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:10]2[CH:33]=[CH:32][C:13]3[N:14]([C:17]4[N:22]=[C:21]([NH:23][C@H:24]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH3:25])[CH:20]=[N:19][CH:18]=4)[CH:15]=[N:16][C:12]=3[CH:11]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10094853HCID 10094853, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10002649HCID 10002649, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-{5-[(4-methylpiperazin-1-yl)carbonyl]-1H-benzimidazol-1-yl}-N-[(1S)-1-phenylethyl]pyrazin-2-amine (22 mg, 0.05 mmol) in dry THF (1 mL) was added to a suspension of LiAlH4 (4 mg, 0.1 mmol) in THF (1 mL) and the mixture heated at reflux for 4 h. Upon cooling to RT, the solution was treated consecutively with H2O (1 mL), aqueous NaOH (1 mL, 2M) and H2O (5 mL). The resulting mixture was extracted with CHCl3 (2×10 mL) and the combined organic layers dried (Na2SO4). The solvent was removed under reduced pressure and the product purified by flash chromatography using CH2Cl2-MeOH (10:1→1:1) as eluant to afford the product as a yellow solid (11 mg, 52%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 h
  3. extractionThe resulting mixture was extracted with CHCl3 (2×10 mL)
  4. dry with materialthe combined organic layers dried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe product purified by flash chromatography

Sources & evidence

ORD record
ord-a4a691d409bb408e962ade6e8704edd6
Source dataset
uspto-grants-2009_03
Patent number
US07511047B2

Reaction notes

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