Methane → HCID 178456073, compound

HRID 865671

Reaction equation

HRID 865671 reaction equation
[C:1]([N:3]=[C:4](OC1C=CC=CC=1)[NH:5][C:6]1[CH:7]=[N:8][C:9]([N:12]([CH3:14])[CH3:13])=[CH:10][CH:11]=1)#[N:2].[C:22]1([C@H:28]([NH2:31])[CH2:29][CH3:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN1CCOCC1.C>C(O)(C)C>[C:1]([N:3]=[C:4]([NH:31][C@@H:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:29][CH3:30])[NH:5][C:6]1[CH:7]=[N:8][C:9]([N:12]([CH3:13])[CH3:14])=[CH:10][CH:11]=1)#[N:2]

Participants

6

Reactant 4

HCID 297MethaneHCID 79724-MethylmorpholineHCID 5324978(R)-1-PhenylpropylamineHCID 178482865HCID 178482865, compound

Product 1

HCID 178456073HCID 178456073, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of the product from Step 4 (2.00 g, 0.00711 mol), (R)-(+)-1-phenylpropylamine (1.06 g, 0.00784 mol), N-methylmorpholine (1.69 ml, 0.0154 mol) and isopropanol (13.3 ml) was refluxed, under nitrogen, until the reaction was shown to be complete by TLC (28 hours). It was then concentrated and the residue chromatographed on silica gel with 1 to 4% MeOH-CHCl3. A solution of the product thus obtained in MeOH-EtOAc was decolorized with Darco (activated charcoal) and crystallized from EtOAc-hexane to give 1.02 g, m.p. 109°-111° C. and 0.120 g, m.p. 107°-113° C. of the titled product.

Workup

  1. customto be complete by TLC (28 hours)
  2. concentrationIt was then concentrated
  3. customthe residue chromatographed on silica gel with 1 to 4% MeOH-CHCl3
  4. customA solution of the product thus obtained in MeOH-EtOAc
  5. customcrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-305b6d1802174bafaad6803f6180f433
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Linked notes

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