Triethylamine → HCID 178425158, compound

HRID 1479776Notes

Reaction equation

HRID 1479776 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[CH3:5].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:32][CH2:33][C:34]1[C:35]([OH:42])=[N:36][C:37]([CH3:41])=[CH:38][C:39]=1[CH3:40]>ClCCl>[OH:42][C:35]1[C:34]([CH2:33][NH:32][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([CH:4]([CH2:3][CH2:2][OH:1])[CH3:5])=[CH:14][CH:13]=2)=[C:39]([CH3:40])[CH:38]=[C:37]([CH3:41])[N:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 89580768HCID 89580768, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425158HCID 178425158, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-hydroxybutan-2-yl)benzoic acid (290 mg, 1.5 mmol), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (432 mg, 2.25 mmol), N-hydroxybenzotriazole (3.4 mg, 2.25 mmol) and triethylamine (455 mg, 4.5 mmol) in dichloromethane (50 mL) was stirred for 30 minutes at room temperature. Then to the mixture, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (228 mg, 1.5 mmol) was added. The resultant mixture was stirred at room temperature for 12 hours. Then the mixture was washed with water (30 mL×3). The organic layer was concentrated to give a residue and the residue was purified by column chromatography (silica gel, dichloro methane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(4-hydroxybutan-2-yl)benzamide (41 mg, 8.3%). LRMS (M+H+) m/z: calcd 328.18 found 328; 1H. NMR (300 MHz, CD3OD): δ 7.73 (d, J=8.1 Hz, 2H), 7.30 (d, J=8.1 Hz, 2H), 6.11 (s, 1H), 4.49 (s, 2H), 3.44-3.42 (m, 2H), 2.94 (q, J=7.2 Hz, 1H), 2.36 (s, 3H), 2.42 (s, 3H), 1.82 (q, J=6.9 Hz, 2H), 1.26 (d, J=6.9 Hz, 3H).

Workup

  1. washThen the mixture was washed with water (30 mL×3)
  2. concentrationThe organic layer was concentrated
  3. customto give a residue
  4. customthe residue was purified by column chromatography (silica gel, dichloro methane/methanol=20:1)

Sources & evidence

ORD record
ord-44a276e9472e42a1be09764c8bfd20d2
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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