Triethylamine → HCID 178425201, compound

HRID 1501231Notes

Reaction equation

[C:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11](C(O)=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].Cl.CN(C)[CH2:22][CH2:23][CH2:24]N=C=NCC.[OH:31]N1C2C=CC=CC=2N=N1.NCC1[C:44]([OH:51])=[N:45][C:46](C)=CC=1C.C([N:54]([CH2:57][CH3:58])[CH2:55][CH3:56])C>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:15][CH:16]=2)[C:44]([NH:45][CH2:46][C:58]2[C:57]([OH:31])=[N:54][C:55]([CH3:56])=[CH:22][C:23]=2[CH3:24])=[O:51])=[CH:17][CH:18]=1)#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

4-(4-cyanophenoxy)benzoic acid (45 mg, 0.19 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (47 mg, 0.25 mmol), 1-Hydroxybenzotriazole (33 mg, 0.25 mmol), triethylamine (00.1 mL) in dichloromethane (5 mL) were stirred at 25° C. for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (50 mg, 0.33 mmol) was added to the above mixture. The mixture was stirred at 25° C. overnight and purified by column chromatography (silica gel, dichloromethane/methanol=12:1) to give 3-(4-cyanophenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (17 mg, 25%). LRMS (M+H+) m/z: 373.14. found 373. HPLC Purity (214 nm): 94%. 1H NMR (300 MHz, DMSO): δ 11.47 (s, 1H), 8.38 (s, 1H), 7.94-7.84 (m, 4H), 7.17-7.13 (m, 4H), 5.85 (s, 1H), 4.29 (d, J=4.5 Hz, 2H), 2.17-2.09 (m, 6H).

Workup

custompurified by column chromatography (silica gel, dichloromethane/methanol=12:1)

Sources & evidence

ORD record: ord-bf415c270bf842ca85a22b85372a4c64
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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