Serinol → HCID 178520896, compound

HRID 1453577Notes

Reaction equation

HRID 1453577 reaction equation
[N:1]1([C:10]2[N:18]=[C:17](Cl)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH2:20][CH:21]([CH2:24][OH:25])[CH2:22][OH:23]>CS(C)=O>[N:1]1([C:10]2[N:18]=[C:17]([NH:20][CH:21]([CH2:24][OH:25])[CH2:22][OH:23])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 68294SerinolHCID 178478376HCID 178478376, compound

Product 1

HCID 178520896HCID 178520896, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

200 mg of product obtained in stage 1 above are mixed with 3 ml of DMSO and 336 mg (5 equivalents) of 2-amino-1,3-propanediol, and the mixture is then heated at 120° C. for approximately 72 hours. The mixture is allowed to return to ambient temperature. Purification is carried out by chromatography on silica with a CH2Cl2-MeOH—NH4OH: 90-9-1 mixture for eluent. Evaporation is carried out and a paste is formed in methylene chloride-methanol: 50-50. Partial drying and drying under vacuum at 50° C. are carried out. 91.4 mg of expected product are obtained.

Workup

  1. customto return to ambient temperature
  2. customPurification
  3. customEvaporation
  4. customa paste is formed in methylene chloride-methanol
  5. customPartial drying
  6. customdrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-88f6cae4df8b464eb7001b527d507e5f
Source dataset
uspto-grants-2009_01
Patent number
US07476670B2

Reaction notes

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