Triethylamine → Quinoline-6-carboxylic acid cyanomethyl-amide

HRID 2079982Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:15][CH2:16][C:17]#[N:18].F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O.C(OCC)(=O)C>[C:16]([CH2:17][NH:18][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13])#[N:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of quinoline-6-carboxylic acid (500 mg, 2.9 mmol) and amino acetonitrile hydrochloride (320 mg, 3.4 mmol) in N,N-dimethylformamide (10 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (1.5 g, 3.48 mmol) and triethylamine (1.2 mL, 8.7 mmol), and the solution was stirred at 60° C. for 10 minutes. Ethyl acetate and water was added to the reaction solution, which was then partitioned, the organic layer was washed twice with water. Silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purified by NH silica gel column chromatography (ethyl acetate), and the title compound (420 mg, 2.0 mmol, 68.9%) was obtained as a light brown solid.

Workup

customwas then partitioned
washthe organic layer was washed twice with water
additionSilica gel was added to the organic layer
customthe solvent was evaporated in vacuo for adsorption
custompurified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-03ffffbe175744569397c4bac26ba816
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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