Acetonitrile → HCID 86599843, compound

HRID 2099021Notes

Reaction equation

HRID 2099021 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[C:12]([OH:18])[CH:11]=2)[CH2:6][CH2:5]1.C[O:20][C:21](=O)[CH2:22][C:23]1[N:24]=[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]2[CH:32]=1.C(#N)C.N1CCCCC1>C1C=CC=CC=1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]2[N:26]([CH:32]=[C:23]([C:22]3[C:21](=[O:20])[O:18][C:12]4[C:13]([CH:14]=3)=[CH:16][CH:17]=[C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][F:1])[CH2:5][CH2:6]3)[CH:11]=4)[N:24]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8082PiperidineHCID 11470752HCID 11470752, compoundHCID 16413490HCID 16413490, compound

Product 1

HCID 86599843HCID 86599843, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

253 mg (1 mmol) 4-[4-(2-Fluoro-ethyl)-piperazin-1-yl]-2-hydroxy-benzaldehyde and 450 mg (2 eq.) (6-chloro-imidazo[1,2-a]pyridin-2-yl)-acetic acid methyl ester refluxed in 15 mL benzene and 7.5 mL acetonitrile in the presence of 0.395 mL (4 eq.) piperidine for 21 h. The reaction mixture is cooled to 0° C. and the precipitated material filtered, washed with diethyl ether and dried under high vacuum, yielding 100 mg (23%) desired product as a yellow solid. M.p.=265° C. (decomposition).

Workup

  1. filtrationthe precipitated material filtered
  2. washwashed with diethyl ether
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-521455caad8c415796162a02be19875e
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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