Acetic Acid → HCID 11373273, compound

HRID 1671648Notes

Reaction equation

HRID 1671648 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-e2b7b088abae4a139b360d54737abe36
Source dataset
uspto-grants-2011_08
Patent number
US07994333B2

Reaction notes

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