Propanal → HCID 58460181, compound

HRID 1946513Notes

Reaction equation

HRID 1946513 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8](=O)[C:7]=1O)[CH3:2].C([O-])(=O)C.[NH4+:19].[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.[CH:29]1([CH:34]=O)[CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)CC>C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:26]2[C:7]3[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:11][CH2:10][CH2:9][C:8]=3[N:19]=[C:34]2[CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 527PropanalHCID 660364-ChlorobenzylamineHCID 70106CyclopentanecarbaldehydeHCID 517165Ammonium AcetateHCID 58460212HCID 58460212, compound

Product 1

HCID 58460181HCID 58460181, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

Intermediate 45 (0.396 g), ammonium acetate (0.154 g), 4-chloro-benzylamine (0.292 ml), were mixed in chloroform (2 mL), to this mixture was added cyclopentanecarbaldehyde (427 ul), propanal (0.144 ml), acetic acid (0.572 ml) and heated to 140° C. (Biotage Initiator) for 20 minutes. The compound was reduced in vacuo and purified with column chromatography. Title compound (170 mg). LC/MS MH+401, Rt 2.47 min (5 min run, TFA modifier).

Workup

  1. custompurified with column chromatography
  2. custom401, Rt 2.47 min (5 min run, TFA modifier)

Sources & evidence

ORD record
ord-0374842ea80449dfbb5dcb303191c9cb
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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