Sulfamic Acid → HCID 67386112, compound

HRID 1898653Notes

Reaction equation

HRID 1898653 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:12]1[N:13]=[C:14]3[C:20]([CH:21]=[O:22])=[CH:19][N:18]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]3=[N:16][CH:17]=1)[C:6]2=[O:11].S(=O)(=O)([OH:33])N.[O-]Cl=O.[Na+].OP([O-])(O)=O.[K+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:12]1[N:13]=[C:14]3[C:20]([C:21]([OH:33])=[O:22])=[CH:19][N:18]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]3=[N:16][CH:17]=1)[C:6]2=[O:11]

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 58438637HCID 58438637, compound

Product 1

HCID 67386112HCID 67386112, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (265 mg, 0.60 mmol) in 1,4-dioxane (35 mL) at 0° C. was added a solution of sulfamic acid (349 mg, 3.59 mmol) in water (4.35 mL. Then a solution of NaClO2 (88 mg, 0.78 mmol) and KH2PO4 (977 mg, 7.18 mmol) in water (8.7 mL) was added via dropping funnel over 15 min. The ice bath was removed and the yellow cloudy reaction mixture was stirred at r.t. for 18 h. The reaction mixture was diluted with water and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4 and concentrated to give 269 mg (98%) of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid which was used without further purification.

Workup

  1. customover 15 min
  2. customThe ice bath was removed
  3. customthe yellow cloudy reaction mixture
  4. extractionextracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0acd1091820a4accbcae1562a5f5b029
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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