Ethyl chloroformate → HCID 13885671, compound

HRID 1709630Notes

Reaction equation

HRID 1709630 reaction equation
C(O[C:4]([NH:6][C:7]1[N:17]=[CH:16][CH:15]=[CH:14][C:8]=1[C:9]([O:11]CC)=O)=[O:5])C.NC1N=CC=CC=1C(OCC)=O.ClC(OCC)=O.C(N(CC)C(C)C)(C)C.[NH2:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][CH:51]([C:54](=[O:62])[C:55]2[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=2)[CH2:50][CH2:49]1>C1(C)C=CC=CC=1.CO>[F:61][C:58]1[CH:57]=[CH:56][C:55]([C:54]([CH:51]2[CH2:50][CH2:49][N:48]([CH2:47][CH2:46][N:45]3[C:9](=[O:11])[C:8]4[CH:14]=[CH:15][CH:16]=[N:17][C:7]=4[NH:6][C:4]3=[O:5])[CH2:53][CH2:52]2)=[O:62])=[CH:60][CH:59]=1

Participants

8

Reactant 5

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 3019268(1-(2-Aminoethyl)piperidin-4-yl) (4-fluorophenyl) ketoneHCID 12433260Ethyl 2-aminopyridine-3-carboxylateHCID 13885651HCID 13885651, compound

Product 1

HCID 13885671HCID 13885671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2.06 g of ethyl 2-ethoxycarbonylaminonicotinate (m.p. 60°, obtainable by boiling ethyl 2-aminonicotinate with ethyl chloroformate for 5 h in the presence of N,N-diisopropylethylamine in toluene) and 2.54 g of 1-(2-aminoethyl)-4-p-fluorobenzoylpiperidine (Rf 0.43 on silica gel with butanol/ethanol/water/ethyl acetate/acetic acid 50:50:50:25:25) is heated at 190° for 1 h. The mixture is cooled and taken up in methanol and, on cooling, 3-[2-(4-p-fluorobenzoylpiperidino)ethyl]-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine is obtained, m.p. 237°. Hydrochloride m.p. 297°-298°. Fumarate m.p. 253°-255°.

Workup

  1. customfor 5 h
  2. temperatureis heated at 190° for 1 h
  3. temperatureThe mixture is cooled
  4. temperatureon cooling

Sources & evidence

ORD record
ord-4d808bb82dce45efbf573c76693a4225
Source dataset
uspto-grants-1990_08
Patent number
US04950648

Reaction notes

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