Dimethylformamide → HCID 89690493, compound

HRID 1481874Notes

Reaction equation

HRID 1481874 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=3[CH3:24])[CH2:13][CH2:12]2)[C:8]([N+:25]([O-:27])=[O:26])=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C)C=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:66][N:67]([CH2:69][C:70]1[CH:71]=[C:72]([CH:75]=[CH:76][CH:77]=1)[CH2:73][NH2:74])[CH3:68]>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=3[CH3:24])[CH2:13][CH2:12]2)[C:8]([N+:25]([O-:27])=[O:26])=[CH:7][C:3]=1[C:4]([NH:74][CH2:73][C:72]1[CH:75]=[CH:76][CH:77]=[C:70]([CH2:69][N:67]([CH3:68])[CH3:66])[CH:71]=1)=[O:5]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162280701-[3-(Aminomethyl)phenyl]-N,N-dimethylmethanamineHCID 89690453HCID 89690453, compound

Product 1

HCID 89690493HCID 89690493, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 40 ml scintillation vial equipped with a magnetic stir bar and a nitrogen inlet, the 2-chloro-4-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-5-nitro-benzoic acid 12b (157.90 mg, 0.41 mmol) was taken up in clean, dry N,N-dimethylformamide (5.00 ml, 64.57 mmol) and the reaction mixture was stirred under nitrogen at room temperature until all solids had gone into solution. To the reaction was then added the HATU (184.80 mg, 0.49 mmol) followed by the N,N-diisopropylethylamine (0.14 ml, 0.80 mmol) and the mixture was stirred until all solids had gone into solution. The 3-dimethylaminomethyl-benzylamine (86.50 mg, 0.53 mmol) was then added to the reaction solution and the reaction was allowed to stir at room temperature overnight. The reaction was diluted with 15 ml of water and 15 ml of ethyl acetate. The layers were then separated and the product was extracted from the aqueous using ethyl acetate (3×20 ml). The organic phases were combined, washed with brine (1×25 ml) and with saturated aqueous lithium chloride solution (2×25 ml). The product solution was then dried over Na2SO4; the solution was then decanted and the solvent was removed under reduced pressure. The crude product, 2-chloro-N-(3-dimethylaminomethyl-benzyl)-4-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-5-nitro-benzamide 13a (214.40 mg, 0.40 mmol), was isolated as an amber oil and was carried on without further purification. LCMS (m/e)=537 (M+H).

Workup

  1. customIn a 40 ml scintillation vial equipped with a magnetic stir bar and a nitrogen inlet
  2. stirringthe mixture was stirred until all solids
  3. stirringto stir at room temperature overnight
  4. customThe layers were then separated
  5. extractionthe product was extracted from the
  6. washwashed with brine (1×25 ml) and with saturated aqueous lithium chloride solution (2×25 ml)
  7. dry with materialThe product solution was then dried over Na2SO4
  8. customthe solution was then decanted
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-70e2269eb8cc4a53b08561ea8832061f
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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