1-Hydroxybenzotriazole → HCID 59625339, compound

HRID 2192785Notes

Reaction equation

HRID 2192785 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=[C:10]([S:17][CH3:18])[N:9]=1.[NH:19]1[CH2:23][CH2:22][CH:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:24][CH:21]1[CH2:22][CH2:23][N:19]([C:14]([C:13]2[C:8]([NH:7][CH2:6][C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[N:9][C:10]([S:17][CH3:18])=[N:11][CH:12]=2)=[O:16])[CH2:20]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 28905833HCID 28905833, compound

Product 1

HCID 59625339HCID 59625339, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-[(2-furylmethyl)amino]-2-(methylthio)pyrimidine-5-carboxylic acid (19.1 mg) and tert-butyl pyrrolidin-3-ylcarbamate (13.4 mg) in DMF (1.0 ml) was added a solution of HOBt (9.7 mg) and WSC.HCl (13.8 mg) in DMF (0.5 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 2% aqueous sodium hydrogen carbonate, the mixture was extracted with ethyl acetate, and the extract was concentrated by a nitrogen gas blower. The residue was purified by reversed-phase preparative HPLC, and the object fraction was concentrated by a nitrogen gas blower. The residue was dissolved in trifluoroacetic acid/acetonitrile solution (20% (V/V), 1.0 ml), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was passed through a column of MP-TsOH resin (manufactured by Argonaut) to fix the object compound on the resin, and the resin was washed with methanol (6 ml). 2 M Ammonia-methanol solution (6 ml) was passed through the column, and the eluate was concentrated by a nitrogen gas blower to give the object compound (6.3 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationthe extract was concentrated by a nitrogen gas blower
  3. customThe residue was purified by reversed-phase preparative HPLC
  4. concentrationthe object fraction was concentrated by a nitrogen gas blower
  5. dissolutionThe residue was dissolved in trifluoroacetic acid/acetonitrile solution (20% (V/V), 1.0 ml)
  6. stirringthe mixture was stirred at room temperature for 3 hr
  7. washthe resin was washed with methanol (6 ml)
  8. concentrationthe eluate was concentrated by a nitrogen gas blower

Sources & evidence

ORD record
ord-90cda38b24c3449cb8fa4b6e21f152df
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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