1-Hydroxybenzotriazole → HCID 59441658, compound

HRID 1014327Notes

Reaction equation

HRID 1014327 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH2:37]([N:40]([CH2:46][CH2:47][CH3:48])[C@H:41]([C:43](O)=[O:44])[CH3:42])[CH2:38][CH3:39]>C1COCC1.C(OCC)(=O)C>[CH3:42][C@H:41]([N:40]([CH2:37][CH2:38][CH3:39])[CH2:46][CH2:47][CH3:48])[C:43]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:6][CH2:7]1)=[O:44]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14274716N,N-Dipropyl-L-alanineHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 59441658HCID 59441658, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (0.8 g, 4.12 mmol) in THF (200 mL) was added EDC hydrochloride (2.37 g, 12.4 mmol), HOBT (1.67 g, 12.4 mmol), and N,N-dipropyl-L-alanine (2.14 g, 12.4 mmol). After stirring at rt for 5 days, the reaction was diluted with ethyl acetate (100 mL), washed with saturated NaHCO3 (200 mL) and 1M NaOH (200 mL). The organic layer was separated, adsorbed onto silica gel, and purified by column chromatography (DCM to 5% MeOH/DCM) to provide N-{(1S)-1-methyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-N-propyl-1-propanamine (0.6 g, 42%). ESIMS (M+H)+=350.

Workup

  1. washwashed with saturated NaHCO3 (200 mL) and 1M NaOH (200 mL)
  2. customThe organic layer was separated
  3. custompurified by column chromatography (DCM to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-b2dacd15c9a04f42843387c6d11ef28e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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