Triethylamine → HCID 69203390, compound

HRID 2377237Notes

Reaction equation

HRID 2377237 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH2:4][CH2:3]1.Cl.[CH3:15][NH:16][CH3:17].O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:15][N:16]([CH3:17])[C:11]([C:6]1[C:5]2[CH2:4][CH2:3][C:2](=[O:1])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:13]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 125422061-Oxo-indan-4-carboxylic acid

Product 1

HCID 69203390HCID 69203390, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 5 (300 mg, 1.70 mmol) in N,N-dimethylformamide (3 mL) was added dimethyl amine hydrochloride (139 mg, 1.70 mmol), 1-hydroxybenzotriazole hydrate (253 mg, 1.87 mmol), triethylamine (0.48 mL, 3.4 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (358 mg, 1.87 mmol). The reaction mixture was stirred at room temperature overnight, quenched by addition of saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using dichloromethane/methanol (20:1) as the mobile phase to provide the desired product. MS (APCI): m/z 204 (M+H)+.

Workup

  1. customquenched by addition of saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-cc4168def8124a6bb3383dad98b91de7
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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