Benzylamine → HCID 67212258, compound

HRID 554599Notes

Reaction equation

HRID 554599 reaction equation
[CH2:1]([N:8]([CH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[Br:24])[C:18]([OH:20])=O)[C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[CH2:40]([NH2:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl.O.CN1C(=O)CCC1.CN(C=O)C>[CH2:40]([NH:47][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:23]([Br:24])=[C:15]([CH2:14][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]([CH:11]2[CH2:12][CH2:13]2)=[O:10])[CH:16]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

9

Reactant 4

HCID 7504BenzylamineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 58565108HCID 58565108, compound

Product 1

HCID 67212258HCID 67212258, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-bromo-benzoic acid (0.1 g, 0.26 mmol) and catalytic DMF (0.01 mL) were combined in CH2Cl2 (4 mL) at room temperature. Oxalyl chloride (0.03 mL, 0.33 mmol) was added, and the reaction was stirred for 30 minutes. The solution was concentrated and dried under vacuum, and then NMP (3 mL) and diisopropylethylamine (0.14 mL, 0.78 mmol) were added. Benzylamine (0.04 mL, 0.39 mmol) was then added, and the reaction was stirred for 5 minutes. The mixture was poured into H2O and partitioned with 1:1 EtOAc:hexanes. The organic layer was washed with saturated aqueous NaHCO3, H2O, and dilute brine, and then dried, filtered, and concentrated to give N-benzyl-3-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-bromo-benzamide.

Workup

  1. concentrationThe solution was concentrated
  2. customdried under vacuum
  3. stirringthe reaction was stirred for 5 minutes
  4. custompartitioned with 1:1 EtOAc
  5. washThe organic layer was washed with saturated aqueous NaHCO3, H2O, and dilute brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-efd90fa628b849328803d7060bcc51ec
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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