Hydrochloric Acid → HCID 9824500, compound

HRID 1760649Notes

Reaction equation

HRID 1760649 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[NH:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)=[O:18])=[O:10])=[N:6][CH:7]=1.N[C:28]1[CH:33]=CC(Cl)=[CH:30][N:29]=1.C[Al](C)C.Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[NH:16][C:17]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[N:29]([CH3:30])[CH2:28][CH2:33][N:26]=3)=[CH:23][CH:24]=2)=[O:18])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 661742-Amino-5-chloropyridineHCID 16682925Trimethylaluminum2×HCID 22596372HCID 22596372, compound

Product 1

HCID 9824500HCID 9824500, compoundYield 80%

Procedure

Preparation of methyl 3-[(4-cyanophenyl)carbonylamino]thiophene-2-carboxylate A mixture of 4-cyanobenzoyl chloride (1.0500 g, 6.4 mmol), methyl 3-aminothiophenecarboxylate (1.0000 g, 6.4 mmol), and triethylamine (1 mL, 7.0 mmol) in dichloromethane was stirred at room temperature for 18 hours. The mixture was poured into a separatory funnel and washed by 1 N HCl. The organic layers were combined, dried over MgSO4, concentrated in vacuo, and chromatographed through a silica gel column to give the title compound 1.6588 g (91%). ES-MS 287 (M+1). Preparation of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl](3-thienyl)}(4-cyanophenyl)carboxamide A portion of 2-amino-5-chloropyridine (68.6 mg, 0.5 mmol) was treated with AlMe3 (0.8 mL, 1.6 mmol), followed by adding the product from step A (160 mg, 0.5 mmol). The mixture was stirred at room temperature for 18 hours. The excess of AlMe3 was killed by 1N HCl solution. The organic layers were combined, dried over MgSO4, concentrated in vacuo, and chromatographed through a silica gel column to give the title compound 0.1528 g (80%). ES-MS 383 (M+1).

Workup

  1. dry with materialdried over MgSO4
  2. concentrationconcentrated in vacuo
  3. customchromatographed through a silica gel column

Sources & evidence

ORD record
ord-e385e13b4b1d4beaa0454e4b6d2bd04a
Source dataset
uspto-grants-2005_01
Patent number
US06844367B1

Reaction notes

Loading…