Benzenemethanamine, 4-chloro-N-methyl- → N-(4-Chloro-benzyl)-2-(3,4-dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-N-methyl-butyramide

HRID 734280Notes

Reaction equation

HRID 734280 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)[C:10](O)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:47][C:48]1[CH:56]=[CH:55][C:51]([CH2:52][NH:53][CH3:54])=[CH:50][CH:49]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:47][C:48]1[CH:56]=[CH:55][C:51]([CH2:52][N:53]([CH3:54])[C:10](=[O:11])[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 66905Benzenemethanamine, 4-chloro-N-methyl-HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 578435372-(3,4-Dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-butyric acid2×

Product 1

HCID 25127969N-(4-Chloro-benzyl)-2-(3,4-dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-N-methyl-butyramideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 25 mg 2-(3,4-dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-butyric acid (intermediate 1), 24.1 mg (0.075 mmol) TBTU, 11.67 mg (0.075 mmol) (4-chloro-benzyl)-methyl-amine (commercially available) and 0.06 mL N,N-diisopropyl ethylamine in 0.75 mL DMF was shaken at room temperature and subsequently subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 20.7 mg (67%) of the title compound as yellow viscous oil. MS(m/e): 534.2 (MH+).

Workup

  1. customsubsequently subjected to purification by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and NEt3
  4. additionThe product containing fractions
  5. customwere evaporated

Sources & evidence

ORD record
ord-b10a0871b43f41fc9bc67b86a493b4bd
Source dataset
uspto-grants-2009_09
Patent number
US07592345B2

Reaction notes

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