Triethylamine → HCID 85049354, compound

HRID 1182457Notes

Reaction equation

HRID 1182457 reaction equation
[CH3:1][C:2](=[CH:8][CH:9]([CH3:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=1)[CH:3]=[CH:4][C:5](O)=[O:6].O.[OH:22][N:23]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.NO.CCN(CC)CC>CN(C=O)C>[OH:22][NH:23][C:5](=[O:6])[CH:4]=[CH:3][C:2]([CH3:1])=[CH:8][CH:9]([CH3:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 72480337HCID 72480337, compound

Product 1

HCID 85049354HCID 85049354, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of carboxylic acid 37 (70 mg, 0.256 mmol) at rt in anhydrous DMF (2 mL) was added 1-hydroxybenzotriazole hydrate (41.5 mg, 0.307 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride(65 mg, 0.340 mmol). After 1 h, hydroxylamine hydrochloride (89 mg, 1.28 mmol) and Et3N (0.27 mL, 1.92 mmol) was added, and stirring was continued at rt overnight. The solvent was removed in vacuo, and the residue was diluted with ethyl acetate (30 mL), and washed with water and saturated NaHCO3 solution (5 mL). After drying and concentration, the crude product was purified by flash silica gel chromatography (2-10% methanol in chloroform) to give the title compound 38 (30 mg, 41% yield) as a yellow oil: 1H NMR (300 MHz, CDCl3:CD3OD=5:1) δ 7.10 (d, J=14.4 Hz, 1H), 6.88 (d, J=8.7 Hz, 2H), 6.58 (d, J=8.7 Hz, 2H), 5.59 (d, J=9.3 Hz, 1H), 5.55 (br. d, J=14.4 Hz, 1H), 2.78 (s, 6H), 2.63 (m, 1H), 2.40 (d, J=6.9 Hz, 2H), 1.48 (s, 3H), 0.89 (d, J=6.6 Hz, 3H); 13C NMR (75 MHz, CDCl3: CD3OD=5:1) δ 11.8, 19.7, 35.3, 40.8, 42.0, 14.3, 20.0, 35.5, 40.8, 42.2, 113.1, 113.7, 128.7, 129.5, 131.1, 145.9, 146.3, 148.9, 165.5.

Workup

  1. waitwas continued at rt overnight
  2. customThe solvent was removed in vacuo
  3. additionthe residue was diluted with ethyl acetate (30 mL)
  4. washwashed with water and saturated NaHCO3 solution (5 mL)
  5. customAfter drying
  6. concentrationconcentration
  7. customthe crude product was purified by flash silica gel chromatography (2-10% methanol in chloroform)

Sources & evidence

ORD record
ord-4bbd52f2cf2a435d991f63d9b28d11de
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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