Water → HCID 86603768, compound

HRID 226461Notes

Reaction equation

Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[N:8][C:9]=1[NH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Cl)[CH:26]=1.C(N(CC)C(C)C)(C)C.O>CN(C=O)C.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[N:8][C:9]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([Cl:24])[CH:26]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of ethyl (2E)-3-[5-chloro-6-(4-piperidinylamino)-3-pyridinyl]acrylate dihydrochloride (500 mg) in DMF (5 ml) was added 1-chloro-3-(chloromethyl)benzene (0.173 ml) and N,N-diisopropylethylamine (0.91 ml), the mixture was stirred at 70° C. for 7 hour. The mixed solution was poured into a mixture of water (30 ml) and AcOEt (30 ml). The organic layer was separated, washed with water twice and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with 5% MeOH in dichloromethane to give ethyl (2E)-3-(5-chloro-6-{[1-(3-chlorobenzyl)-4-piperidinyl]amino}-3-pyridinyl)acrylate (261 mg, 46%).

Workup

customThe organic layer was separated
washwashed with water twice
dry with materialbrine, dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography
washeluted with 5% MeOH in dichloromethane

Sources & evidence

ORD record: ord-5e1c1910cc35485fbdd1b01824823346
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557127B2

Reaction notes

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