Dimethylformamide → HCID 59170835, compound

HRID 1446471Notes

Reaction equation

HRID 1446471 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:20]#[C:21][C:22]([OH:24])=O)[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1.[NH2:25][CH:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)(Cl)Cl.O>[CH:37]1[C:38]2[CH:26]([NH:25][C:22](=[O:24])[C:21]#[C:20][C:10]3[CH:11]=[CH:12][C:13]([N:14]4[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]4)=[C:8]([O:7][CH3:6])[CH:9]=3)[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]=2[CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10671Fluoren-9-amineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66961695HCID 66961695, compound

Product 1

HCID 59170835HCID 59170835, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A DMF (2 mL) solution of [3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]propiolic acid (74 mg) and 9-aminofluorene (65 mg) and BOP (133 mg) and N,N′-IPEA (77 μL) was agitated at room temperature overnight. Water and chloroform were added to the reaction solution, the organic layer was partitioned and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent:heptane-ethyl acetate system), and 45 mg of the title compound was obtained.

Workup

  1. customthe organic layer was partitioned
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent:heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-8ac96debac1545f29ac9cff05e719848
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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