Triethylamine → 3-Oxo-3-[N'-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carbonyl)-hydrazino]-propionic acid tert-butyl ester

HRID 6916Notes

Reaction equation

HRID 6916 reaction equation
NN.[C:3]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:4][C:5]([O-:7])=O.[OH2:14].O[N:16]1[C:20]2[CH:21]=CC=CC=2N=[N:17]1.[CH2:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH3:26].Cl.CN(C)[CH2:35][CH2:36][CH2:37][N:38]=C=NCC>ClCCl>[C:10]([O:9][C:3](=[O:8])[CH2:4][C:5](=[O:7])[NH:17][NH:16][C:20]([CH:21]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[CH:35][CH:36]=[CH:37][N:38]=2)[CH2:25][CH2:26]1)=[O:14])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 9321HydrazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21883978Tert-butyl malonate

Product 1

HCID 235440723-Oxo-3-[N'-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carbonyl)-hydrazino]-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the hydrazine from preparation 35 (2.2 g, 10 mmol), tert-butyl malonate (1.6 g, 10 mmol), 1-hydroxybenzotriazole hydrate (2.02 g, 15 mmol), triethylamine (4.8 ml, 20 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.4 g, 12.5 mmol) in dichloromethane (50 ml) was stirred at room temperature for 5 hours. The reaction was diluted with dichloromethane (200 ml), washed with water (150 ml), dried (MgSO4) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using ethyl acetate as eluant to afford the title compound, as a white solid, 1.4 g.

Workup

  1. washwashed with water (150 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residual oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2ff387fd184f4f2e8c6f2f73124e8925
Source dataset
uspto-grants-2006_08
Patent number
US07084145B2

Reaction notes

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