2-Ethyl butylamine → Benzyl-1-(2-(2-ethylbutylamino)-2-oxoethyl)-2-oxo-1,2-dihydropyridin-3-yl-carbamate

HRID 58315Notes

Reaction equation

HRID 58315 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:22])[N:14]([CH2:18][C:19]([OH:21])=O)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:64]([CH:66]([CH2:69][CH3:70])[CH2:67][NH2:68])[CH3:65]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]1[C:13](=[O:22])[N:14]([CH2:18][C:19]([NH:68][CH2:67][CH:66]([CH2:69][CH3:70])[CH2:64][CH3:65])=[O:21])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 120492-Ethyl butylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 186721592-(3-(((Benzyloxy)carbonyl)amino)-2-oxopyridin-1(2H)-yl)acetic acid

Product 1

HCID 118104219Benzyl-1-(2-(2-ethylbutylamino)-2-oxoethyl)-2-oxo-1,2-dihydropyridin-3-yl-carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.70 g of 2-(3-(benzyloxycarbonylamino)-2-oxopyridin-1(2H)-yl)acetic acid (˜11.2 mmol), 3.58 g of TBTU (11.2 mmol), 1.51 g of HOBt (11.2 mmol) is dissolved in 60 mL of DMF. By addition of 5.70 mL of DIPEA (33.5 mmol, 3 eq) a pH value is adjusted to ˜10. 1.50 mL of 2-ethyl-butylamine (11.2 mmol) is added and the mixture is stirred at RT overnight. The solvent is removed in vacuo and the obtained residue is taken up in 300 mL of DCM and subsequently washed with 10% citric acid (3×75 mL), saturated NaHCO3 solution (3×75 mL) and brine (75 mL). The organic phase is dried over Na2SO4, filtered and concentrated in dryness. Pale brown solid is obtained and it is suitable for further processing without further purification.

Workup

  1. customThe solvent is removed in vacuo
  2. washsubsequently washed with 10% citric acid (3×75 mL), saturated NaHCO3 solution (3×75 mL) and brine (75 mL)
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in dryness
  6. customPale brown solid is obtained
  7. customit is suitable for further processing without further purification

Sources & evidence

ORD record
ord-95502cae39944280b66e93911e468eb4
Source dataset
uspto-grants-2016_09
Patent number
US09434763B2

Reaction notes

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