Pentylamine → HCID 66819205, compound

HRID 1617146Notes

Reaction equation

HRID 1617146 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:7]([O:9][C:10](=[O:27])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]2[C:19](Cl)=[N:20][C:21]([NH2:25])=[N:22][C:23]=2[CH3:24])[CH:12]=1)[CH3:8]>CN1C(=O)CCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:7]([O:9][C:10](=[O:27])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]2[C:23]([CH3:24])=[N:22][C:21]([NH2:25])=[N:20][C:19]=2[NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:12]=1)[CH3:8]

Participants

6

Reactant 2

HCID 8060PentylamineHCID 86633397HCID 86633397, compound

Product 1

HCID 66819205HCID 66819205, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
150 °C

Procedure

Pentylamine (2.5 mL) was added to a stirred solution of the product from step (ii) (1.65 g) in NMP (3 mL). The mixture was heated at 150° C. for 15 h and allowed to cool. The solution was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL) added. The aqueous phase was separated and the organic phase washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography eluting with 2% to 5% MeOH in DCM to give the subtitle compound as an orange solid. 0.7 g.

Workup

  1. temperatureto cool
  2. additionadded
  3. customThe aqueous phase was separated
  4. washthe organic phase washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by chromatography
  8. washeluting with 2% to 5% MeOH in DCM

Sources & evidence

ORD record
ord-c4ec72c8c0394e648ed4237ba5ea464c
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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