Diisopropylethylamine → HCID 178454173, compound

HRID 254368Notes

Reaction equation

HRID 254368 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][C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.I.[NH2:37][C:38]1[C:39]([C:46]([NH:48][C:49](=[NH:52])SC)=[O:47])=[N:40][C:41]([Cl:45])=[C:42]([NH2:44])[N:43]=1>C(O)C>[C:23]([O:22][C:20]([NH:19][C@H:15]([CH2:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:49]([NH2:52])=[N:48][C:46]([C:39]2[C:38]([NH2:37])=[N:43][C:42]([NH2:44])=[C:41]([Cl:45])[N:40]=2)=[O:47])=[CH:7][CH:8]=1)[C:16]([OH:18])=[O:17])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58664828HCID 58664828, compoundHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178454173HCID 178454173, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

The compound 280 (0.077 g, 0.211 mmol) was mixed with ethanol (5 mL). The mixture was heated at 65° C. for 15 min to achieve complete dissolution. To the clear solution were sequentially added diisopropylethylamine (0.184 mL, 1.056 mmol) and 1-(3,5-diamino-6-chloropyrazinoyl)-2-methylisothiourea hydriodide (0.99 g, 0.254 mmol). The mixture was heated at 65° C. for an additional three hours. It was then concentrated under vacuum. The residue was chromatographed over silica gel, eluting with a mixture of concentrated ammonium hydroxide (0-2.2%), methanol (0-22%) and dichloromethane (100-75.8%) to afford the product 290 (0.091 g, 75%) as a yellow solid. 1H NMR (300 MHz, CD6OD): δ 1.44 (s, 9H), 1.58-1.84 (m, 8H), 2.54-2.68 (m, 4H), 3.34-3.42 (m, 2H), 4.02 (m, 1H), 7.08 (s, 4H). m/z (APCI) 577 [C26H37ClN8O5+H]+.

Workup

  1. dissolutiondissolution
  2. temperatureThe mixture was heated at 65° C. for an additional three hours
  3. concentrationIt was then concentrated under vacuum
  4. customThe residue was chromatographed over silica gel
  5. washeluting with a mixture of concentrated ammonium hydroxide (0-2.2%), methanol (0-22%) and dichloromethane (100-75.8%)

Sources & evidence

ORD record
ord-4ce5b890831d40239e291db2fefdaaf1
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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