Dimethylformamide → HCID 54675676, compound

HRID 2203330Notes

Reaction equation

HRID 2203330 reaction equation
CN(C=O)C.[NH2:6][C:7]1[C:8]2[C:36]([CH3:43])([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:35](=[O:44])[NH:34][C:9]=2[N:10]=[C:11]([NH:13]/[N:14]=[C:15](\[C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2Br)/[CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=2[F:25])[N:12]=1.CNCCNC>CCOC(C)=O.[Cu]I>[NH2:6][C:7]1[C:8]2[C:36]([CH3:43])([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:35](=[O:44])[NH:34][C:9]=2[N:10]=[C:11]([N:13]2[C:27]3[C:26](=[CH:31][C:30]([Cl:32])=[CH:29][CH:28]=3)[C:15]([CH2:16][C:17]3[C:22]([F:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=3[F:25])=[N:14]2)[N:12]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8070N,N'-DimethylethylenediamineHCID 89438492HCID 89438492, compound

Product 1

HCID 54675676HCID 54675676, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A DMF (5 mL) solution of the crude intermediate from Step C (ca 0.24 mmol), copper (I) iodide (45.3 mg, 0.24 mmol) and N,N′-dimethylethylenediamine (25.2 mg, 0.29 mmol) was stirred at ambient temperature for 1 hour. The reaction mixture was diluted with EtOAc and washed with 10% aqueous NH4OH solution (2×), water (2×), 0.5 N HCl (1×), and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by preparative thin layer chromatography using 5% MeOH/CHCl3 as eluent. The isolated material was purified again by silica gel column chromatography using a hexanes/EtOAc gradient to give the indicated compound. 1H NMR (500 MHz, DMSO-d6): δ (ppm) 11.19 (1H, s), 8.86 (1H, d, J=9.0 Hz), 7.93 (1H, d, J=2.0 Hz), 7.55-7.43 (2H, m), 7.34-7.24 (5H, m), 7.20 (1H, t, J=9.7 Hz), 6.74 (2H, s), 4.46 (2H, s), 1.77 (3H, s). m/z=535.4 (M+H).

Workup

  1. washwashed with 10% aqueous NH4OH solution (2×), water (2×), 0.5 N HCl (1×), and brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin layer chromatography
  6. customThe isolated material was purified again by silica gel column chromatography
  7. customto give the indicated compound

Sources & evidence

ORD record
ord-6c3c45dc63e248c8a3528cf746cd60aa
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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