N,N,N',N',N'',N''-Hexamethylmethanetriamine → HCID 178462501, compound

HRID 1988768Notes

Reaction equation

HRID 1988768 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]([CH2:9][CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=O)=[N:8][C:4]=2[CH:3]=1.CN(C([N:31]([CH3:33])C)N(C)C)C.C(O)(=O)C.[NH2:38]N>CCO>[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]([CH2:9][C:10]3[C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=4)=[N:38][NH:31][CH:33]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 165591Hydrazine, acetate (1:1)HCID 22379891HCID 22379891, compound

Product 1

HCID 178462501HCID 178462501, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(5-Bromo-1-ethyl-1H-benzoimidazol-2-yl)-1-(3-fluoro-phenyl)-propan-1-one (0.1 g, 0.27 mmol) and tris(dimethylamino)methane (0.077 g, 0.54 mmol) is heated at 60° C. in a sealed tube for 6 hours. The volatile material is removed in vacuo. EtOH (5 mL) and hydrazine acetate (1.1 mmol) are added to the residue. The mixture is heated at 120° C. for 2 hours. The solvent is removed. NaHCO3 (aq.) (10 mL) and DCM (30 mL) are added to the residue. The organic layer is separated and the aqueous layer is extracted with DCM (2×15 mL). The combined organic layers are dried and the solvent removed. The crude is purified by PTLC (ethyl acetate/Hexanes 1:1) to give 5-bromo-1-ethyl-2-[3-(3-fluoro-phenyl)-1H-pyrazol-4-ylmethyl]-1H-benzoimidazole as a solid. LRMS: calcd 399.3. found [M+1] 401.0.

Workup

  1. customThe volatile material is removed in vacuo
  2. temperatureThe mixture is heated at 120° C. for 2 hours
  3. customThe solvent is removed
  4. additionNaHCO3 (aq.) (10 mL) and DCM (30 mL) are added to the residue
  5. customThe organic layer is separated
  6. extractionthe aqueous layer is extracted with DCM (2×15 mL)
  7. customThe combined organic layers are dried
  8. customthe solvent removed
  9. customThe crude is purified by PTLC (ethyl acetate/Hexanes 1:1)

Sources & evidence

ORD record
ord-881ad4064a8949c899bb04dc9d992b0e
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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