Diisopropylethylamine → (S,E)-Ethyl 6-(tert-butoxycarbonylamino)-7-(1-(2-(2-ethylbutylamino)-2-oxoethyl)-2-oxo-1,2-dihydropyridin-3-ylamino)-7-oxohept-2-enoate

HRID 58324Notes

Reaction equation

HRID 58324 reaction equation
[NH2:1][C:2]1[C:3](=[O:18])[N:4]([CH2:8][C:9]([NH:11][CH2:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:19]([O:23][C:24]([NH:26][C@@H:27]([CH2:31][CH2:32]/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:28](O)=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:19]([O:23][C:24]([NH:26][C@H:27]([C:28]([NH:1][C:2]1[C:3](=[O:18])[N:4]([CH2:8][C:9]([NH:11][CH2:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:10])[CH:5]=[CH:6][CH:7]=1)=[O:29])[CH2:31][CH2:32]/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:25])([CH3:20])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 899258912-(3-Amino-2-oxopyridin-1(2H)-yl)-N-(2-ethylbutyl)acetamideHCID 89926005(S,E)-2-(tert-butoxycarbonylamino)-7-ethoxy-7-oxohept-5-enoic acid

Product 1

HCID 118104221(S,E)-Ethyl 6-(tert-butoxycarbonylamino)-7-(1-(2-(2-ethylbutylamino)-2-oxoethyl)-2-oxo-1,2-dihydropyridin-3-ylamino)-7-oxohept-2-enoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 101 mg of 2-(3-amino-2-oxopyridin-1(2H)-yl)-N-(2-ethyl-butyl)acetamide (2a, 0.40 mmol) in 2.5 mL of DMF is provided. To this solution, a solution of 121 mg of (S,E)-2-(tert-butoxycarbonylamino)-7-ethoxy-7-oxohept-5-enoic acid (ZED775, 0.40 mmol), 152 mg of HATU (0.40 mmol) and 136 μL of DIPEA (2 eq) in 2.5 mL of DMF is added. By successive addition of DIPEA the pH value is adjusted to ca. 7. The reaction mixture is stirred at 40° C. for 1.5 hours and subsequently at RT overnight, before the solvent is removed in vacuo. The obtained residue is taken up in 75 mL of ethyl acetate and subsequently washed each three times with 10% citric acid, saturated NaHCO3 solution and brine. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo in dryness. Gel is obtained and it is suitable for further processing without further purification.

Workup

  1. customis removed in vacuo
  2. washsubsequently washed each three times with 10% citric acid, saturated NaHCO3 solution and brine
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo in dryness
  6. customGel is obtained
  7. customit is suitable for further processing without further purification

Sources & evidence

ORD record
ord-4e3c77f125e74b6aaed8858ca960daec
Source dataset
uspto-grants-2016_09
Patent number
US09434763B2

Reaction notes

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