Hydrochloric Acid → HCID 135407816, compound

HRID 1947205Notes

Reaction equation

HRID 1947205 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([O:11]CC=C)[C:8]([CH2:15][C:16]#[C:17][CH3:18])=[CH:7][C:6]=1[C:19]1[N:20]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:27][CH:26]=2)[C:21](=[O:24])[NH:22][N:23]=1)C=C.C(=O)([O-])[O-].[K+].[K+].O.Cl>CO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:15]([C:8]1[C:9]([OH:11])=[CH:10][C:5]([OH:4])=[C:6]([C:19]2[N:20]([C:25]3[CH:26]=[CH:27][C:28]([CH2:31][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:29][CH:30]=3)[C:21](=[O:24])[NH:22][N:23]=2)[CH:7]=1)[C:16]#[C:17][CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 59829889HCID 59829889, compound

Product 1

HCID 135407816HCID 135407816, compoundYield 21.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere crude 5-[2,4-bis-allyloxy-5-(but-2-ynyl)-phenyl]-4-[4-(morpholin-4-ylmethyl)-phenyl]-2,4-dihydro-[1,2,4]triazol-3-one(F470-IM12: 208 mg) was dissolved in methanol (10 mL) and mixed with potassium carbonate (348 mg, 2.52 mmol) and tetrakis (triphenylphosphine) palladium (20 mg, 0.016 mmol), and the mixture was heated for 3 hours under reflux. After adding water (5 mL), the reaction mixture was adjusted to pH 6.5 with 2M hydrochloric acid. Silica gel (2.0 g) was added to this mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol=30:1-10:1) to obtain the title compound (OH-c02: 38 mg, yield 10.4%, in 4 steps).

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. additionSilica gel (2.0 g) was added to this mixture
  4. concentrationthe mixture was concentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform-methanol=30:1-10:1)

Sources & evidence

ORD record
ord-e96ee0d660dc447fa44ac068fc2a870a
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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