Methyl 4-aminobenzoate → Methyl 4-(3-carbamoyl-6-chloropyridin-2-ylamino)benzoate

HRID 2044055Notes

Reaction equation

HRID 2044055 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[NH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[C:4]([C:3]1[C:2]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)=[N:10][C:9]([Cl:11])=[CH:8][CH:7]=1)(=[O:5])[NH2:6]

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 2733832Lithium HexamethyldisilazideHCID 221427782,6-Dichloropyridine-3-carboxamide

Product 1

HCID 57489609Methyl 4-(3-carbamoyl-6-chloropyridin-2-ylamino)benzoateYield 106.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichloronicotinamide (1 g, 5.24 mmol) and methyl 4-aminobenzoate (0.950 g, 6.28 mmol) in THF (30 mL) was added lithium bis(trimethylsilyl)amide (18.32 mL, 18.32 mmol) at −78° C. The reaction mixture was stirred for 10 min. The dry ice bath was removed and the reaction mixture was stirred at rt for 3.5 h. The reaction mixture was diluted with water and the resulting yellow precipitate was filtered to give 1.7 g of methyl 4-(3-carbamoyl-6-chloropyridin-2-ylamino)benzoate as a yellow solid.

Workup

  1. customThe dry ice bath was removed
  2. stirringthe reaction mixture was stirred at rt for 3.5 h
  3. additionThe reaction mixture was diluted with water
  4. filtrationthe resulting yellow precipitate was filtered

Sources & evidence

ORD record
ord-2c9f538eea7a403fa08c4879b2378aab
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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