HCID 19041500, compound → HCID 19041587, compound

HRID 1683896Notes

Reaction equation

HRID 1683896 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:22][CH2:23][CH3:24])[CH:6]2[CH2:17][C:16]3[CH:15]=[C:14]4[C:10]([C:11]([C:18](=O)[CH2:19][CH3:20])=[CH:12][NH:13]4)=[CH:9][C:8]=3[CH2:7]2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH:1]1([CH2:4][N:5]([CH2:22][CH2:23][CH3:24])[CH:6]2[CH2:17][C:16]3[CH:15]=[C:14]4[C:10]([C:11]([CH2:18][CH2:19][CH3:20])=[CH:12][NH:13]4)=[CH:9][C:8]=3[CH2:7]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 19041500HCID 19041500, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19041587HCID 19041587, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1-[6-(cyclopropylmethyl-propyl-amino)-1,5,6,7-tetrahydro-1-aza-s-indacen-3-yl]-propan-1-one (12h, Chart 2) (58 mg, 0.18 mmol) in dry diethyl ether (4 mL) was added in small portions lithium aluminum hydride (40 mg, 1.06 mmol). The reaction mixture was stirred over night and then quenched by the consecutive addition of water (40 μL), 15% sodium hydroxide (40 μL) and water (120 μL). After stirring for 15 min., the solid material was filtered off and the solvent removed in vacuo to yield a residue of 28 mg (50%) of the title compound.

Workup

  1. customquenched by the consecutive addition of water (40 μL), 15% sodium hydroxide (40 μL) and water (120 μL)
  2. stirringAfter stirring for 15 min.
  3. filtrationthe solid material was filtered off
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f4fed8e900d346e2ac858f4e1cb0119a
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

Loading…