Acetic Anhydride → HCID 68747606, compound

HRID 1396612Notes

Reaction equation

HRID 1396612 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](/[C:12](=[N:14]/[OH:15])/[NH2:13])=[N:9][C:8]([C@@H:16]([NH:18][C:19]1[N:27]=[CH:26][N:25]=[C:24]3[C:20]=1[N:21]=[CH:22][N:23]3[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH3:17])=[CH:7]2.[C:37](OC(=O)C)(=O)[CH3:38]>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]1[N:13]=[C:37]([CH3:38])[O:15][N:14]=1)=[N:9][C:8]([C@@H:16]([NH:18][C:19]1[N:27]=[CH:26][N:25]=[C:24]3[C:20]=1[N:21]=[CH:22][N:23]3[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[CH3:17])=[CH:7]2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 136381035HCID 136381035, compound

Product 1

HCID 68747606HCID 68747606, compound

Procedure

(S,Z)-8-chloro-N′-hydroxy-3-(1-((9-(4-methoxybenzyl)-9H-purin-6-yl)amino)ethyl)isoquinoline-1-carboximidamide 30 (502 mg, 1 mmol, 1.0 eq) was dissolved in acetic anhydride (10 mL) and the resulting mixture was stirred at reflux overnight. The mixture was cooled to RT and concentrated in vacuo to remove acetic anhydride. The resulting suspension was diluted with water (50 mL) and neutralized with concentrated ammonium hydroxide to adjust the pH value to 7-8. The mixture was extracted with DCM (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (1-10% MeOH-DCM) to afford the product ((S)—N-(1-(8-chloro-1-(5-methyl-1,2,4-oxadiazol-3-yl)isoquinolin-3-yl)ethyl)-9-(4-methoxybenzyl)-9H-purin-6-amine 31.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. customto remove acetic anhydride
  4. additionThe resulting suspension was diluted with water (50 mL) and neutralized with concentrated ammonium hydroxide
  5. extractionThe mixture was extracted with DCM (3×100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by flash column chromatography on silica gel (1-10% MeOH-DCM)

Sources & evidence

ORD record
ord-845d363a34b74843b39313f741544aa8
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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