Phosphorus sulfide (P2S5) → 5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazole-2-carboxylic acid methyl ester

HRID 644057Notes

Reaction equation

HRID 644057 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]([NH:6][CH2:7][C:8]([C:10]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:11]=1)=O)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:30]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1[S:30][C:8]([C:10]2[C:18]3[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:11]=2)=[CH:7][N:6]=1)=[O:28]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 68693889N-[(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-2-oxo-ethyl]oxalamic acid methyl ester

Product 1

HCID 687007055-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazole-2-carboxylic acid methyl esterYield 98.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-[(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-2-oxo-ethyl]-oxalamic acid methyl ester (429 mg, 1.11 mmol) in chloroform (20 ml) was added phosphorus pentasulfide (538 mg, 1.21 mmol) and the reaction mixture heated at reflux for 3.5 h. The reaction mixture was cooled, poured into a separating funnel and washed with water and then brine. The organic layers were then dried over magnesium sulfate, filtered and the solvent removed in vacuo. The resulting solid was purified by flash column chromatography eluting with dichloromethane to give 5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazole-2-carboxylic acid methyl ester (418 mg, 1.09 mmol) as a brown solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 3.5 h
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into a separating funnel
  5. washwashed with water
  6. dry with materialThe organic layers were then dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe resulting solid was purified by flash column chromatography
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8bd9412e0c304c57909011c5fbbb5892
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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