Toluene → HCID 117849241, compound

HRID 1477724Notes

Reaction equation

HRID 1477724 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:37]=[CH:36][C:12]([CH2:13][N:14]2[CH:19]=[N:18][C:17]([NH:20][CH:21]3[CH2:25][CH2:24][C:23]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)(O)[CH:22]3[OH:34])=[N:16][C:15]2=[O:35])=[CH:11][CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[Cl:8][C:9]1[CH:37]=[CH:36][C:12]([CH2:13][N:14]2[CH:19]=[N:18][C:17]([NH:20][CH:21]3[CH2:25][CH:24]=[C:23]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH:22]3[OH:34])=[N:16][C:15]2=[O:35])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 117839216HCID 117839216, compound

Product 1

HCID 117849241HCID 117849241, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A toluene solution (200 μL) of 1-(4-chlorobenzyl)-4-{[3-(4-fluorophenyl)-2,3-dihydroxycyclopentyl]amino}-1,3,5-triazin-2(1H)-one (14.0 mg, 0.0325 mmol) synthesized in Synthesis Example 465 and p-toluenesulfonic acid monohydrate (6.18 mg, 0.0325 mmol) was stirred at 100° C. for 8 hours. After the completion of the reaction, to the reaction solution, triethylamine was added and the reaction solution was concentrated under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography (chloroform/ethyl acetate=1/2) to obtain the title compound (7.00 mg, yield: 52%).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customby purifying the resultant residue by silica gel column chromatography (chloroform/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-ca80c285c3b04aa193900a08e677ab9d
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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