Isopropanol → HCID 86618509, compound

HRID 1254127Notes

Reaction equation

HRID 1254127 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].Cl[C:8]1[N:13]=[CH:12][C:11]2[C:14](=[C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[O:15][CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[C:9]=1[Cl:33].[CH:34](O)(C)C>>[Cl:33][C:9]1[C:10]2[CH:16]([C:17]([CH:22]=[CH:21][CH3:34])=[CH:18][CH:19]=[CH2:20])[O:15][C:14](=[C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[C:11]=2[CH:12]=[N:13][C:8]=1[NH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 735613-Amino-1,2-propanediolHCID 76798890HCID 76798890, compound

Product 1

HCID 86618509HCID 86618509, compoundYield 50%

Procedure

A solution of 3-amino-propane-1,2-diol (225 mg, 2.47 mmol) in 4 mL of isopropanol is treated with 3-(6,7-Dichloro-1-phenyl-1H-furo[3,4-c]pyridin-3-ylidene)-1,3-dihydro-indol-2-one (100 mg, 0.25 mmol) in one portion. The reaction mixture is heated to reflux overnight, cooled to room temperature and concentrated. The residue is purified by chromatography (silica gel, gradient elution 5% MeOH/Chloroform to 15% MeOH/Chloroform). The product containing fractions are concentrated to give the title compound as a yellow solid (56 mg, 50%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. customThe residue is purified by chromatography (silica gel, gradient elution 5% MeOH/Chloroform to 15% MeOH/Chloroform)
  5. additionThe product containing fractions
  6. concentrationare concentrated

Sources & evidence

ORD record
ord-17018040030d4d1d91bfcee4cd666d7a
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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