tert-Butyl carbazate → HCID 90036206, compound

HRID 2205666Notes

Reaction equation

HRID 2205666 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]([OH:15])=O)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:38]([O:42][C:43]([NH:45][NH2:46])=[O:44])([CH3:41])([CH3:40])[CH3:39]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]([C:13]([NH:46][NH:45][C:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:44])=[O:15])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 4

HCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 197944512-Methoxyquinoline-3-carboxylic acid

Product 1

HCID 90036206HCID 90036206, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 2-methoxyquinoline-3-carboxylic acid (0.92 g, 4.55 eq) in DCM (45 mL) under N2, HOBT (6.83 mmol, 1.5 eq), EDC.HCl (6.83 mmol, 1.5 eq) triethylamine (5.0 mmol, 1.1 eq) and tert-butylhydrazine carboxylate (5.00 mmol, 1.1 eq) were added. The mixture was stirred at room temperature for 3 h, diluted with DCM and washed with sat. aq. NaHCO3 and sat. aq. NaCl. The organic phase was dried (Na2SO4), concentrated under reduced pressure and the product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc 9:1 to 0:100) affording 1.23 g of product as a white solid (85% yield). MS (ES) C16H19N3O4 requires: 317.34, found: 318.

Workup

  1. washwashed with sat. aq. NaHCO3 and sat. aq. NaCl
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customthe product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc 9:1 to 0:100)

Sources & evidence

ORD record
ord-7f18af6b09ed4fdb9559394fa2152aa2
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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