Formaldehyde → HCID 11855214, compound

HRID 900688Notes

Reaction equation

HRID 900688 reaction equation
[CH2:1]=O.[CH2:3]([NH:7][CH3:8])[CH2:4][CH2:5][CH3:6].[Cl:9][C:10]1[C:11]([N:30]2[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]2)=[N:12][CH:13]=[C:14]([C:16](=[O:29])[NH:17][C:18]2[S:19][CH:20]=[C:21]([C:23]3[S:24][CH:25]=[C:26]([Cl:28])[CH:27]=3)[N:22]=2)[CH:15]=1>C(O)(=O)C>[CH2:3]([N:7]([CH2:1][C:20]1[S:19][C:18]([NH:17][C:16]([C:14]2[CH:15]=[C:10]([Cl:9])[C:11]([N:30]3[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]3)=[N:12][CH:13]=2)=[O:29])=[N:22][C:21]=1[C:23]1[S:24][CH:25]=[C:26]([Cl:28])[CH:27]=1)[CH3:8])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8068N-MethylbutylamineHCID 23117190HCID 23117190, compound

Product 1

HCID 11855214HCID 11855214, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

3 ml of acetic acid, 24 μl of a formaldehyde aqueous solution (36%) and 47 μl of N-butyl-N-methylamine were added to 150 mg of ethyl 1-(3-chloro-5-{[4-(4-chlorothiophen-2-yl)thiazol-2-yl]carbamoyl}-2-pyridyl)piperidine-4-carboxylate, and the mixture was stirred at 90° C. for 18 hours. After the solvent was distilled off under reduced pressure, a saturated sodium hydrogencarbonate aqueous solution was added. The mixture was extracted with chloroform, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using hexane:EtOAc (7:1 to 5:1) as an elution solvent to obtain 147 mg of ethyl 1-(5-{[5-{[butyl(methyl)amino]methyl}-4-(4-chlorothiophen-2-yl)thiazol-2-yl]carbamoyl}-3-chloro-2-pyridyl)piperidine-4-carboxylate.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. additiona saturated sodium hydrogencarbonate aqueous solution was added
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee0ac52932074f1e810e2b90ce4a0c38
Source dataset
uspto-grants-2008_04
Patent number
US07361658B2

Reaction notes

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