Ethanol → HCID 178500880, compound

HRID 254357Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[CH:4]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.[NH2:36][C:37]1[CH:38]=[N:39][C:40]([Cl:44])=[C:41]([NH2:43])[N:42]=1.I.CS[C:48](=[NH:50])[NH2:49].[CH2:51]([OH:53])C>>[CH3:1][O:2][C:3](=[O:26])[CH:4]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:48]([NH2:49])=[N:50][C:51]([C:38]2[C:37]([NH2:36])=[N:42][C:41]([NH2:43])=[C:40]([Cl:44])[N:39]=2)=[O:53])=[CH:11][CH:12]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 81531Diisopropylethylamine

HCID 66849895HCID 66849895, compound

HCID 86606144HCID 86606144, compound

Product 1

HCID 178500880HCID 178500880, compoundYield 37%

Conditions

Temperature: 65 °C

Procedure

Compound 103 (366 mg, 0.99 mmol) was dissolved in ethanol (8 mL) then diisopropylethyl amine (0.86 mL, 4.9 mmol) and 1-(3,5-diamino-6-chloropyrazine-2-methyl-isothiourea hydriodide (407 mg, 1.04 mmol) were added and the reaction was heated to 65° C. for 1.5 h. The solvents were removed under reduced pressure and the residue was purified by column chromatography (silica gel, eluent: 90:10:1, v/v dichloromethane/methanol/conc. ammonium hydroxide) to provide compound 104 (215 mg, 37%). 1H NMR (300 MHz, DMSO-d6) δ 9.13 (m, 1H), 8.89 (m, 1H), 8.70 (m, 1H), 7.45 (m, 4H), 7.13 (d, 2H), 6.85 (d, 2H), 4.43 (m, 1H), 4.17 (m, 2H), 3.68 (s, 3H), 3.30 (m, 2H), 2.90 (m, 1H), 2.56 (m, 2H), 1.58 (m, 4H), 1.40 (s, 9H). m/z (APCI) 579 [C25H35ClN8O6+H]+. Rf=0.65 (85:15:1 dichloromethane/methanol/conc. ammonium hydroxide).

Workup

customThe solvents were removed under reduced pressure
customthe residue was purified by column chromatography (silica gel, eluent: 90:10:1, v/v dichloromethane/methanol/conc. ammonium hydroxide)

Sources & evidence

ORD record: ord-ea0a3ccd53f04f928b578d79d1b9e0eb
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875619B2

Reaction notes

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