4-Acetamidobenzaldehyde → HCID 21906630, compound

HRID 1247087Notes

Reaction equation

HRID 1247087 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5].[C:19]([NH:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)(=[O:21])[CH3:20].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[B-][N+](C)(C)C>C(O)(=O)C.CO.C1(C)C=CC=CC=1>[C:19]([NH:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:1][C:2]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=2[C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=2)=[O:5])=[CH:25][CH:24]=1)(=[O:21])[CH3:20]

Participants

8

Reactant 4

HCID 739424-AcetamidobenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 21906630HCID 21906630, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a small sample of 2-amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide (0.01 g, 0.035 mmol) weighed out in a sealable vial toluene was added (200 μL), followed by 4-acetamidobenzaldehyde (0.006 g, 0.035 mmol) and pyridinium p-toluenesulfonate (catalytic amount). A few molecular sieves were added; then the vial was sealed and placed in a shaker at 75° C. After 18 h, the reaction mixture was treated with borane-trimethylamine complex (100 μL of a 1 M solution in acetic acid) and the vial was placed in the shaker at room temperature for an additional 5 h. The reaction mixture was then diluted with methanol and applied to a 0.5 g SCX column, washed with methanol and gravity-eluted with 1 N ammonia in methanol. The product fractions were combined and concentrated in vacuo to a residue which was triturated in acetonitrile to provide the title compound as a yellowish powder (0.015 g, 100%) in 98% purity by LC-MS (method A).

Workup

  1. additionwas added (200 μL)
  2. additionA few molecular sieves were added
  3. customthen the vial was sealed
  4. customplaced in a shaker at 75° C
  5. waitwas placed in the shaker at room temperature for an additional 5 h
  6. washwashed with methanol
  7. washgravity-eluted with 1 N ammonia in methanol
  8. concentrationconcentrated in vacuo to a residue which
  9. customwas triturated in acetonitrile

Sources & evidence

ORD record
ord-cd25769bf24748e19083432c2bf6f0df
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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