Diisopropylethylamine → HCID 178461613, compound

HRID 81326Notes

Reaction equation

HRID 81326 reaction equation
I.[NH2:2][C:3]1[C:4]([C:11]([NH:13][C:14](=[NH:17])SC)=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1.[OH:18][C@@H:19]1[CH2:24][O:23][C@@H:22]([CH3:25])[O:21][C@H:20]1[CH2:26][N:27]([CH2:42][C@H:43]1[C@H:48]([OH:49])[CH2:47][O:46][C@@H:45]([CH3:50])[O:44]1)[CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])=[CH:33][CH:32]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[OH:18][C@@H:19]1[CH2:24][O:23][C@@H:22]([CH3:25])[O:21][C@H:20]1[CH2:26][N:27]([CH2:42][C@H:43]1[C@H:48]([OH:49])[CH2:47][O:46][C@@H:45]([CH3:50])[O:44]1)[CH2:28][CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:14]([NH:13][C:11]([C:4]2[C:3]([NH2:2])=[N:8][C:7]([NH2:9])=[C:6]([Cl:10])[N:5]=2)=[O:12])=[NH:17])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67364433HCID 67364433, compoundHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178461613HCID 178461613, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methylisothiourea hydriodide (0.39 g, 1.0 mmol) was added to a solution of 13 (0.49 g, 1.07 mmol) in THF (8 mL) containing diisopropylethylamine (0.18 mL, 2 mmol). The reaction mixture was stirred at reflux for 2.5 h and at room temperature overnight. After this time, the solvent was removed under reduced pressure. The brown residue was washed with ether (2×30 mL) and methylene chloride (2×10 mL). The residue was dissolved in a minimal volume of methanol (approx. 2 mL) and poured into water. The precipitate was collected, washed with water and dried overnight to give crude 11 (0.5 g) as a yellow solid. The compound 11 (0.4 g, 54%) was purified by flash chromatography on silica gel (eluent: chloroform/methanol/ammonium hydroxide=10:1:0.1) as a yellow solid. [α]D25=−20.4° (c=1.0, MeOH).

Workup

  1. customAfter this time, the solvent was removed under reduced pressure
  2. washThe brown residue was washed with ether (2×30 mL) and methylene chloride (2×10 mL)
  3. dissolutionThe residue was dissolved in a minimal volume of methanol (approx. 2 mL)
  4. additionpoured into water
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried overnight

Sources & evidence

ORD record
ord-59a9ce8f10ca43b8a27cdfbfa2cf229b
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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