Triethylamine → HCID 178494488, compound

HRID 1501089Notes

Reaction equation

[CH3:1][O:2][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:36][CH2:37][C:38]1[C:39]([OH:46])=[N:40][C:41]([CH3:45])=[CH:42][C:43]=1[CH3:44]>ClCCl>[OH:46][C:39]1[C:38]([CH2:37][NH:36][C:8](=[O:10])[C:7]2[CH:6]=[CH:5][C:4]([CH:3]([O:2][CH3:1])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:12][CH:11]=2)=[C:43]([CH3:44])[CH:42]=[C:41]([CH3:45])[N:40]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4-(methoxy(phenyl)methyl)benzoic acid (0.26 g, 1.07 mmol), 1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride (309 mg, 1.61 mmol), 1-hydroxybenzotriazole (218 mg, 1.61 mmol), triethylamine (0.45 mL) and dichloromethane (15 mL) was stirred at 25° C. for half an hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (163 mg, 1.07 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(methoxy(phenyl)methyl)benzamide (Compound I-53) as a white solid (80 mg, 20%). LRMS (M+H+) m/z: calcd 376.18. found 376. HPLC purity (214 nm): 96%. 1H NMR (300 MHz, d6-DMSO): δ 11.43 (s, 1H), 8.25 (t, J=3.6 Hz, 1H), 7.30 (d, J=6.9 Hz, 2H), 7.41-7.18 (m, 7H), 5.95 (s, 1H), 5.83 (s, 1H), 4.27 (d, J=3.6 Hz, 2H), 3.31 (s, 3H), 2.14 (s, 3H), 2.10 (s, 3H).

Workup

stirringThe mixture was stirred at 25° C. for 12 hours
concentrationThe resultant mixture was concentrated
customto give a residue
customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record: ord-4c8c499cedcc42dd86b74b2d34240bcd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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