HCID 21905257, compound → HCID 21905574, compound

HRID 1247420Notes

Reaction equation

HRID 1247420 reaction equation
[NH2:1][C:2]1[C:3]([F:24])=[C:4]([CH:9]([O:22][CH3:23])[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[O:11])[C:5]([F:8])=[CH:6][CH:7]=1>ClCCl>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][NH:12][C:10](=[O:11])[CH:9]([C:4]2[C:5]([F:8])=[CH:6][CH:7]=[C:2]([NH:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:3]=2[F:24])[O:22][CH3:23])=[CH:15][CH:16]=1)#[N:21]

Participants

3

Reactant 1

HCID 21905257HCID 21905257, compound

Product 1

HCID 21905574HCID 21905574, compoundYield 153.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (RS)-2-(3-amino-2,6-difluoro-phenyl)-N-(4-cyano-benzyl)-2-methoxy-acetamide (130 mg) at rt in dichloromethane were added sucessively dry 4A molecular sieves (50 mg), phenyl boronic acid (96 mg), triethylamine (0.11 ml), copper (II) acetate (71 mg) and TEMPO (67 mg). A “CaCl2 trap” was placed over the flask and stirring at rt was continued over the week-end. Then the solids were filtered off and washed with EtOAc. The dark brown filtrate was concentrated to leave a dark brown residue. The crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 3:2) to give (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-phenylamino-phenyl)-2-methoxy-acetamide (123 mg) as light grey gum. MS 408.3 ([M+H]+)

Workup

  1. dry with materialdry 4A molecular sieves (50 mg), phenyl boronic acid (96 mg), triethylamine (0.11 ml), copper (II) acetate (71 mg) and TEMPO (67 mg)
  2. filtrationThen the solids were filtered off
  3. washwashed with EtOAc
  4. concentrationThe dark brown filtrate was concentrated
  5. customto leave a dark brown residue
  6. customThe crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 3:2)

Sources & evidence

ORD record
ord-d4f9d4a2e8014c49bf655db7387dd3e9
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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