Acetohydrazide → HCID 68000416, compound

HRID 931914Notes

Reaction equation

HRID 931914 reaction equation
[CH2:1]([C@H:4]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:28][CH3:29])[C:25](O)=[O:26])[C:5]1=[O:30])[CH:2]=[CH2:3].[C:31]([NH:34][NH2:35])(=[O:33])[CH3:32].Cl.C(N=C=NCCCN(C)C)C.N1C2C(=NC=CC=2)N(O)N=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C=O)C.Cl>[C:31]([NH:34][NH:35][C:25](=[O:26])[C@@H:24]([N:6]1[C@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[CH2:9][C@H:4]([CH2:1][CH:2]=[CH2:3])[C:5]1=[O:30])[CH2:28][CH3:29])(=[O:33])[CH3:32]

Participants

9

Reactant 5

HCID 14039AcetohydrazideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67998533HCID 67998533, compound

Product 1

HCID 68000416HCID 68000416, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 95 mg (0.213 mmol) of (S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoic acid (Example 33, Step A) and acetic hydrazide (23.65 mg, 0.319 mmol) in DCM (479 μL) and DMF (53.2 μL) was treated at 0° C. with N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (122 mg, 0.638 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (87 mg, 0.638 mmol), and sodium bicarbonate (53.6 mg, 0.638 mmol) at 0° C., successively. Then the reaction was stirred at 25° C. for 12 h. The reaction was diluted with 1 N aq. HCl and extracted (2×EtOAc). The combined organic layers were washed with sat. aq. NaCl and NaHCO3-solutions, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification by chromatography on silica gel (60% to 80% EtOAc/Hexanes, gradient elution) provided the title compound as a colorless film. MS (ESI) 502.1 [M+H]+.

Workup

  1. extractionextracted (2×EtOAc)
  2. washThe combined organic layers were washed with sat. aq. NaCl and NaHCO3-solutions
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification by chromatography on silica gel (60% to 80% EtOAc/Hexanes, gradient elution)

Sources & evidence

ORD record
ord-de92d1c5e3c942309a0f8a7b19ca72c8
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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