Methanol → HCID 59725991, compound

HRID 1912871Notes

Reaction equation

HRID 1912871 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:41])[C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:40])[NH:26][C:27]2[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=2)[C:30]([OH:32])=O)=[CH:20][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CO.[NH2:50][CH:51]([CH2:54][OH:55])[CH2:52][OH:53]>ClCCl.O1CCCC1>[C:1]([O:5][C:6](=[O:7])[N:8]([C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25]([NH:26][C:27]2[CH:35]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:33]=[C:29]([C:30](=[O:32])[NH:50][CH:51]([CH2:54][OH:55])[CH2:52][OH:53])[CH:28]=2)=[O:40])=[CH:22][CH:23]=1)[CH3:41])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 68294SerinolHCID 23155131HCID 23155131, compound

Product 1

HCID 59725991HCID 59725991, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In dichloromethane (3.5 mL), 60 mg (0.105 mmol) of 3-(3-{4-[6-(tert-butoxycarbonyl-methylamino)-purin-9-yl]phenyl}ureido)-5-(trifluoromethyl)benzoic acid was dissolved, and 54.9 μL (0.63 mmol) of oxalyl chloride was slowly added thereto and the mixture solution was stirred under refluxing for 1.5 hours. The solvent was distilled under reduced pressure from the reaction solution and the obtained residue was dissolved in tetrahydrofuran (0.75 mL). The tetrahydrofuran solution thus prepared was added dropwise to a methanol (0.5 mL)/tetrahydrofuran (0.25 mL) solution of 28.7 mg (0.315 mmol) of 2-amino-1,3-propanediol and the resulting solution was stirred at room temperature for 1.5 hours. The solvent was distilled under reduced pressure from the reaction solution and the obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 5:1) to obtain 40.8 mg (60%) of a target product as a white solid.

Workup

  1. temperatureunder refluxing for 1.5 hours
  2. distillationThe solvent was distilled under reduced pressure from the reaction solution
  3. dissolutionthe obtained residue was dissolved in tetrahydrofuran (0.75 mL)
  4. customThe tetrahydrofuran solution thus prepared
  5. stirringthe resulting solution was stirred at room temperature for 1.5 hours
  6. distillationThe solvent was distilled under reduced pressure from the reaction solution
  7. customthe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 5:1)

Sources & evidence

ORD record
ord-d0c66fa5a5f94ac5a362286c77fe57b3
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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