Dimethylformamide → HCID 18931391, compound

HRID 1599006Notes

Reaction equation

HRID 1599006 reaction equation
[NH2:1][C:2]1([C:23]([NH2:25])=[O:24])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])=[O:13])[CH2:4][CH2:3]1.[C:26](N1C=CN=C1)(N1C=CN=C1)=[S:27].CN(C=O)C>O>[Cl:20][C:18]1[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[C:14]([C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][N:5]2[CH2:4][CH2:3][C:2]3([NH:1][C:26](=[S:27])[NH:25][C:23]3=[O:24])[CH2:7][CH2:6]2)[CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 18931229HCID 18931229, compound

Product 1

HCID 18931391HCID 18931391, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-amino-1-[5-(5-chloro-2-methoxyphenyl)-5-oxopentyl]-piperidine-4-carboxamide (0.36 g, 1 mmol), prepared as in Example 21, 1,1'-thiocarbonyldiimidazole (0.23 g, 1.3 mmol), and DMF (3 mL) was heated 5 hours at 50°-60° C. and then diluted with water. The mixture was extracted with ethyl acetate and the extract was dried (MgSO4) and concentrated. The residue was purified by column chromatography eluting with methylene chloride/methanol+ammonium hydroxide (95:5) to give 8-[5-(5-chloro-2-methoxyphenyl)-5-oxopentyl]-2-thioxo-1,3,8-triazaspiro[4.5]decane-4-one (0.12 g, 0.29 mmol), m.p. 152°-154° C. (dec).

Workup

  1. temperaturewas heated 5 hours at 50°-60° C.
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extract was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol+ammonium hydroxide (95:5)

Sources & evidence

ORD record
ord-9df70334b30e4d6f9c7d5723c02a81d1
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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