2,4-Dichlorobenzylamine → HCID 58460196, compound

HRID 1946509Notes

Reaction equation

HRID 1946509 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].C(=O)[CH2:12][CH:13]([CH3:15])[CH3:14].C([O-])(=O)C.[NH4+:21].[CH2:22]([O:24][C:25](=[O:35])[CH2:26][C:27]1[CH2:32][CH2:31][CH2:30][C:29](=O)[C:28]=1O)[CH3:23]>C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][N:5]1[C:28]2[CH:27]([CH2:26][C:25]([O:24][CH2:22][CH3:23])=[O:35])[CH2:32][CH2:31][CH2:30][C:29]=2[N:21]=[C:12]1[CH:13]([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 14852,4-DichlorobenzylamineHCID 115523-MethylbutanalHCID 517165Ammonium AcetateHCID 58460212HCID 58460212, compound

Product 1

HCID 58460196HCID 58460196, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

2,4-dichlorobenzyl amine (0.080 mL), isovaleraldehyde (0.046 mL), ammonium acetate (38.5 mg), Intermediate 45 (99 mg) and acetic acid (0.143 mL) were mixed in chloroform (1 mL) and heated to 140° C. (Biotage Initiator) for 20 minutes. The mixture was purified by MDAP (Method C). The appropriate fractions were passed through SCX (5 g) and washed with methanol. The products were collected by elution in 2M ammonia in methanol. Title compound (35 mg). LC/MS MH+ 409, Rt 2.38 min (5 min run, TFA modifier).

Workup

  1. customThe mixture was purified by MDAP (Method C)
  2. washwashed with methanol
  3. customThe products were collected by elution in 2M ammonia in methanol
  4. customLC/MS MH+ 409, Rt 2.38 min (5 min run, TFA modifier)

Sources & evidence

ORD record
ord-d822ba4860fc42db9af875faeac8e1e6
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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