Water → HCID 66965198, compound

HRID 1514897Notes

Reaction equation

HRID 1514897 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH:4]=O.[NH2:11][C:12]1[CH:13]=[C:14]([CH:26]=[CH:27][C:28]=1[NH2:29])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([CH3:25])[CH:19]=1)=[O:16].C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>CS(C)=O.CCOC(C)=O>[CH3:25][C:20]1[CH:19]=[C:18]([NH:17][C:15]([C:14]2[CH:26]=[CH:27][C:28]3[N:29]=[C:4]([C:3]4[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:2]=4[Cl:1])[NH:11][C:12]=3[CH:13]=2)=[O:16])[CH:23]=[CH:22][C:21]=1[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 2733225Ytterbium triflate2×HCID 124670502-Chloro-6-methylbenzaldehydeHCID 66965643HCID 66965643, compound

Product 1

HCID 66965198HCID 66965198, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-6-methylbenzaldehyde (107 mg) and 3,4-diamino-N-(3,4-dimethylphenyl)-benzamide (Example 5-1, step 6) (160 mg) in DMSO (1.5 mL) was added Yb(OTf)3 (80 mg). The solution was stirred at room temperature for 18 h then an additional 40 mg of Yb(OTf)3 was added the mixture was stirred at 70° C. for 24 h. The mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified by flash chromatography using hexanes/ethyl acetate (5:1) and the product was isolated as a foam. MS (m/z) 390 (M+1), retention time=1.66 min, Method 10.

Workup

  1. stirringwas stirred at 70° C. for 24 h
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. customthe product was isolated as a foam

Sources & evidence

ORD record
ord-d5950943d7bf4283a23ef17efa2b10f6
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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