1-Hydroxybenzotriazole → HCID 131735818, compound

HRID 2205664Notes

Reaction equation

HRID 2205664 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH2:44][CH2:45][C:46]([C:48]1[C:49]([O:58][CH3:59])=[N:50][C:51]2[C:56]([CH:57]=1)=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])[C:10]([NH:44][CH2:45][C:46]([C:48]1[C:49]([O:58][CH3:59])=[N:50][C:51]2[C:56]([CH:57]=1)=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47])=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11197378HCID 11197378, compoundHCID 900366552-Amino-1-(2-methoxyquinolin-3-yl)ethan-1-one

Product 1

HCID 131735818HCID 131735818, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-((tert-butoxycarbonyl)amino)-8-oxodecanoic acid (0.76 mmol, 1 eq), EDC.HCl (0.99 mmol, 1.3 eq), HOBT (0.99 mmol, 1.3 eq) in DMF (3 mL) was stirred at room temperature for 10 min. A solution of 2-amino-1-(2-methoxyquinolin-3-yl)ethanone (1 eq) in 3 mL of DMF and DIPEA (2 eq) was added and the mixture was stirred at room temperature for 2 h. Mixture was diluted with DCM and washed with brine. The organic phase was dried (Na2SO4), filtered and concentrated. Residue was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 10% EtOAc to 80% EtOAc), to isolate title compound in 20% yield. MS (ES) C27H37N3O6 requires: 499.60, found: 500.

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customResidue was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 10% EtOAc to 80% EtOAc)

Sources & evidence

ORD record
ord-3a01fadd19ff4ec38eade196381cc3c9
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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