Benzenemethanamine, 3-chloro- → HCID 67147426, compound

HRID 2426991Notes

Reaction equation

HRID 2426991 reaction equation
Cl[C:2]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([Cl:26])=[CH:19][C:3]=1[C:4]([NH:6][C@H:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)[CH3:8])=[O:5].[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32]>C1COCC1>[Cl:26][C:20]1[CH:21]=[C:22]([N+:23]([O-:25])=[O:24])[C:2]([NH:32][CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[C:28]([Cl:27])[CH:29]=2)=[C:3]([CH:19]=1)[C:4]([NH:6][C@H:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 57908498HCID 57908498, compound

Product 1

HCID 67147426HCID 67147426, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-{(1S)-1-[(2,5-dichloro-3-nitrobenzoyl)amino]ethyl}benzoate (500 mg, 1.26 mil) and 3-chlorobenzyl amine (1089 mg, 7.69 mmol) were dissolved in 50 ml THF. The mixture was refluxed overnight then cooled. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. 1H NMR (400 MHz, DMSO): δ 9.25 (d, 1H), 8.20 (t, 1H), 8.15 (s, 1H), 7.95 (d, 2H), 7.70 (s, 1H), 7.60 (d, 2H), 7.30 (m, 2H), 7.15 (s, 1H), 7.05 (d, 1H), 5.10 (m, 2H), 4.10 (m, 2H), 4.85 (s, 3H), 1.45 (d, 3H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturethen cooled
  3. customThe solvent was removed
  4. customthe crude mixture purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8cab89ccf7cb4d47986531430747be51
Source dataset
uspto-grants-2011_06
Patent number
US07968578B2

Reaction notes

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