Ethanol → HCID 178512146, compound

HRID 1696853Notes

Reaction equation

HRID 1696853 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22](O)[C:21]=2C)[OH:19])=[CH:8][CH:7]=1.I.[NH2:30][C:31]1[C:32]([C:39]([NH:41][C:42](=[NH:45])SC)=[O:40])=[N:33][C:34]([Cl:38])=[C:35]([NH2:37])[N:36]=1.C(N(C(C)C)CC)(C)C.[CH2:55]([OH:57])C>>[NH2:30][C:31]1[C:32]([C:39]([NH:41][C:42]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C@H:18]([OH:19])[C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH2:55][OH:57])[CH:21]=3)=[CH:10][CH:11]=2)=[NH:45])=[O:40])=[N:33][C:34]([Cl:38])=[C:35]([NH2:37])[N:36]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 66860269HCID 66860269, compoundHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178512146HCID 178512146, compoundYield 5%

Conditions

Temperature
65 °C

Procedure

A solution containing 62 (0.24 g, 0.62 mmol) dissolved in ethanol (8 mL) was heated to 65° C. The reaction mixture was treated with 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (0.24 mg, 0.62 mmol) and diisopropylethylamine (0.47 mL). The reaction mixture was stirred at that temperature for 5 h under N2 atmosphere. The solution was concentrated vacuo. The resulting residue was first purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane, and then further purified by preparative TLC using the same solvent system to afford the desired product 63 (15 mg, 5%) as a pale yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.22 (d, 1H), 7.08 (d, 4H), 6.97 (d, 1H), 6.68 (d, 4H), 6.57 (br, 1H), 4.45 (s, 2H), 3.15 (d, 2H), 2.33 (t, 1H), 1.59-1.52 (m, 6H), 1.39 (s, 2H), 1.23 (s, 1H), m/z (ESI) 600 [C29H39ClN8O4+H]+.

Workup

  1. concentrationThe solution was concentrated vacuo
  2. customThe resulting residue was first purified by column chromatography
  3. washeluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane
  4. customfurther purified by preparative TLC

Sources & evidence

ORD record
ord-6a9ccbd3f84b42618fdcc8050a954bf4
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

Loading…