HCID 10356117, compound → HCID 10093825, compound

HRID 966153Notes

Reaction equation

HRID 966153 reaction equation
Cl[C:2]1[C:7]2=[C:8]([CH:17]([CH3:19])[CH3:18])[C:9]([C:11]3[O:12][C:13]([CH3:16])=[CH:14][N:15]=3)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][C:31]=1[F:32])[C:24]([NH:26][O:27][CH3:28])=[O:25]>CN(C)C=O.C(OCC)(=O)C>[F:32][C:31]1[CH:30]=[CH:29][C:23]([C:24]([NH:26][O:27][CH3:28])=[O:25])=[CH:22][C:21]=1[NH:20][C:2]1[C:7]2=[C:8]([CH:17]([CH3:19])[CH3:18])[C:9]([C:11]3[O:12][C:13]([CH3:16])=[CH:14][N:15]=3)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 10356117HCID 10356117, compoundHCID 223130843-Amino-4-fluoro-N-methoxybenzamide

Product 1

HCID 10093825HCID 10093825, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 58 (30 mg, 0.11 mmol) in dimethyl formamide (0.7 mL) at RT was added 3-amino-4-fluoro-N-methoxy-benzamide (30 mg, 0.16 mmol). After stirring at ambient temperature for 19 h, the mixture was dissolved in ethyl acetate and washed with 10% LiCl solution. The organic layer was separated, dried and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 5% methanol in chloroform to afford the title compound (22 mg, 48%) as an off-white solid. LC/MS; (M+H)+=425.1.

Workup

  1. washwashed with 10% LiCl solution
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-5eb18598a8514e2fbefaea4de1988ec7
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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