Triethylamine → HCID 178474674, compound

HRID 2170503Notes

Reaction equation

HRID 2170503 reaction equation
[C:1]([NH:4][CH:5]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[CH3:6])(=[O:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:35][CH2:36][C:37]1[C:38]([OH:45])=[N:39][C:40]([CH3:44])=[CH:41][C:42]=1[CH3:43]>ClCCl>[C:1]([NH:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:35][CH2:36][C:37]2[C:38]([OH:45])=[N:39][C:40]([CH3:44])=[CH:41][C:42]=2[CH3:43])=[O:13])=[CH:14][CH:15]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18423026HCID 18423026, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178474674HCID 178474674, compoundYield 135.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-(1-acetamidoethyl)benzoic acid (414 mg, 2.0 mmol), 1-hydroxybenzotriozole (405 mg, 3.0 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (576 mg, 3.0 mmol), triethylamine (0.83 mL) in dichloromethane (30 mL) was added 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (82 mg, 0.54 mmol). The reaction mixture was stirred at 20° C. for 13 hours. The mixture was washed with water (20 mL×2). The organic phase was dried over sodium sulfate and filtered. The filtrate was concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give 4-(1-acetamidoethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (250 mg, 37%). LRMS (M+H+) m/z: calcd 341.17. found 341. HPLC Purity (214 nm): 98%. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.35-8.26 (m, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.4 Hz, 2H), 5.85 (s, 1H), 4.90 (q, J=7.2 Hz, 1H), 4.28 (d, J=5.1 Hz, 2H), 2.16 (s, 3H), 2.11 (s, 3H), 1.83 (s, 3H), 1.1 (d, J=7.2 Hz, 3H).

Workup

  1. washThe mixture was washed with water (20 mL×2)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-e95a06dd9b5a42d0b88c02689c5bc809
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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