Acetic Acid → HCID 11373273, compound

HRID 2375576Notes

Reaction equation

HRID 2375576 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[C:20]([OH:21])=[C:19]([C:22]([OH:24])=[O:23])[C:18]3[C:9](=[C:10]4[C:15](=[CH:16][CH:17]=3)[CH2:14][CH2:13][NH:12][CH2:11]4)[N:8]=2)=[CH:4][CH:3]=1.C(O)(=O)C.C(N(CC)CC)C.[O:38]([C:40]#[N:41])[K].N1C=CC=CC=1>>[C:40]([N:12]1[CH2:11][C:10]2[C:15](=[CH:16][CH:17]=[C:18]3[C:9]=2[N:8]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:26][CH:25]=2)[C:20]([OH:21])=[C:19]3[C:22]([OH:24])=[O:23])[CH2:14][CH2:13]1)(=[O:38])[NH2:41]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 1049PyridineHCID 8471TriethylamineHCID 11474129HCID 11474129, compoundHCID 178418250HCID 178418250, compound

Product 1

HCID 11373273HCID 11373273, compoundYield 22.5%

Conditions

Temperature
25 °C

Procedure

A mixture of 2-(4-Chloro-benzyl)-3-hydroxy-7,8,9,10-tetrahydro-(1,9]phenanthroline-4-carboxylic acid (0.213 g, 0.53 mmol), acetic acid (0.6 mL, 5.3 mmol), triethylamine (0.146 mL, 1.06 mmol), KOCN (43 mg, 0.53 mmol), and pyridine (0.84 mL, 5.3 mmol) was stirred at 25° C. overnight. The solid was removed by filtration. HPLC of the mother liquor gave pure product (49.1 mg, 22%) as a beige solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 3.25 (m, 2H), 3.68 (m, 2H), 4.34 (s, 2H), 4.63 (s, 2H), 7.22-7.45 (m, 5H), 8.47 (d, J=9.09 Hz, 1H).

Workup

  1. customThe solid was removed by filtration

Sources & evidence

ORD record
ord-f4dca4d6be454624a9656efe3f7b3a12
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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