Tris(hydroxymethyl)aminomethane → 7-methyl-2-Quinolinecarboxamide

HRID 1244427Notes

Reaction equation

HRID 1244427 reaction equation
C([NH:18]CC=O)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[CH3:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][C:29]([C:33]([OH:35])=O)=[N:30]2)=[CH:25][CH:24]=1.ON1C2C=CC=CC=2N=N1.C(O)C(N)(CO)CO>ClCCl>[CH3:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][C:29]([C:33]([NH2:18])=[O:35])=[N:30]2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 757711-HydroxybenzotriazoleHCID 10858926(9H-Fluoren-9-yl)methyl 2-oxoethylcarbamateHCID 219193287-Methylquinoline-2-carboxylic acid

Product 1

HCID 235320417-methyl-2-QuinolinecarboxamideYield 339.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the amine 4 (1.0 mg, 1.9 μmol, 1.0 equiv) in dichloromethane (0.1 mL) was added to 7-methylquinoline-2-carboxylic acid (2.8 μmol, 1.5 equiv) and 1-hydroxybenzotriazole (0.44 mg, 3.2 μmol, 1.7 equiv) in a vial at 23° C. The solution was stirred for 5 min, then N-cyclohexylcarbodiimide-N′-propyloxymethyl polystyrene (Argonaut Technologies, 1.13 mmol/g, 3.4 mg, 3.8 μmol, 2.0 equiv) was added in one portion at 23° C. The reaction mixture was stirred gently at 23° C. under an argon atmosphere for 16 h. PS-Trisamine (Argonaut Technologies, 4.71 mmol/g, 2.0 mg, 9.5 μmol, 5.0 equiv) was then added in one portion and the reaction mixture was stirred for a further 2 h. The mixture was filtered through Celite (0.5 cm) and concentrated in vacuo to give the 7-methylquinoline-2-carboxylic acid amide derivative (1.2 mg, 95%) as an off-white solid.

Workup

  1. stirringThe reaction mixture was stirred gently at 23° C. under an argon atmosphere for 16 h
  2. stirringthe reaction mixture was stirred for a further 2 h
  3. filtrationThe mixture was filtered through Celite (0.5 cm)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-995aca66a323444badc721d3f5a93460
Source dataset
uspto-grants-2006_10
Patent number
US07122549B2

Reaction notes

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