1,1'-(Azodicarbonyl)dipiperidine → HCID 90052119, compound

HRID 2284706

Reaction equation

HRID 2284706 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([CH2:19]O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[N+:21]([C:24]1[CH:25]=[C:26]([SH:30])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(P(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([CH2:19][S:30][C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 2435763-Nitrobenzene-1-thiolHCID 90052116HCID 90052116, compound

Product 1

HCID 90052119HCID 90052119, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13831TributylphosphineSolvent2×

Procedure

To a solution of (2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)methanol (E13, 20 mg) and 3-nitrothiophenol (17 mg) in tetrahydrofuran (1 mL), tributylphosphine (36 μL) and 1,1′-(azodicarbonyl)dipiperidine (28 mg) were added under ice cooling, and the mixture was stirred at room temperature for 6 hours and 30 minutes. To the reaction mixture, tributylphosphine (36 μL) and 1,1′-(azodicarbonyl)dipiperidine (28 mg) were added at room temperature, and the mixture was stirred at the same temperature for 8 hours and 30 minutes. The solvent was evaporated under reduced pressure, and then the obtained residue was purified by basic silica gel column chromatography (eluent, 88 to 40% hexane in ethyl acetate) to obtain N2-(3-fluorophenyl)-5-(((3-nitrophenyl)thio)methyl)-N4-propylpyrimidine-2,4-diamine (E19, 19 mg) as yellow solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 8 hours and 30 minutes
  2. customThe solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified by basic silica gel column chromatography (eluent, 88 to 40% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-20c14a64133e4d859015f1104817bb2c
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Linked notes

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