4-Methylmorpholine → HCID 136333985, compound

HRID 1630417Notes

Reaction equation

HRID 1630417 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1)([O-:3])=[O:2].C1C=C[C:15]2[N:20](O)N=N[C:16]=2[CH:17]=1.C[CH2:23][N:24]=C=NCCCN(C)C.[CH3:33]N1CCOCC1.[C:40](C(N)(N)C(C)(C)CN)([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH:24][CH2:23][C:16]([CH3:17])([CH3:33])[CH2:15][NH:20][C:40](=[O:41])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:11])[CH:5]=1)([O-:3])=[O:2]

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 53249489HCID 53249489, compoundHCID 862226845-Nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 136333985HCID 136333985, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.00 g of 5-nitro-3-pyrazolecarboxylic acid, 2.24 g of HOBt, 2.81 g of EDCI, 3.86 g of NMM and 2.58 g of 1-Boc-amino-2,2-dimethyl-1,3-propanediamine are dissolved in DMF (30 ml) and the solution is stirred at RT for 8 h. The reaction mixture is admixed with sat. NaHCO3 solution and ethyl acetate. The organic phase is removed and the aqueous phase is extracted three times more with ethyl acetate. The combined organic phases are dried over Na2SO4 and concentrated. The residue is purified by chromatography (silica gel, ethyl acetate:heptane). The 3.21 g of tert-butyl {3-[(5-nitro-1H-pyrazole-3-carbonyl)amino]-2,2-dimethylpropyl}carbamate thus obtained are dissolved in MeOH (20 ml) and admixed with 140 mg of palladium on carbon (10%). Hydrogenation is effected with hydrogen pressure 4.5 bar for 3 h. The solution is filtered and the solvent is removed under reduced pressure.

Workup

  1. customThe organic phase is removed
  2. extractionthe aqueous phase is extracted three times more with ethyl acetate
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography (silica gel, ethyl acetate:heptane)

Sources & evidence

ORD record
ord-fa5fbcd4f9e243dba231a4ce327dccd9
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

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