Sulfamic Acid → HCID 90040555, compound

HRID 523027Notes

Reaction equation

HRID 523027 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:11]([CH:12]=[O:13])=[CH:10][N:9]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]2=[N:6][C:7]=1[Cl:8].S(=O)(=O)([OH:24])N.Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[K+]>O.O1CCOCC1>[Br:1][C:2]1[N:3]=[C:4]2[C:11]([C:12]([OH:24])=[O:13])=[CH:10][N:9]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]2=[N:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 90041493HCID 90041493, compound

Product 1

HCID 90040555HCID 90040555, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-bromo-3-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (1.96 g, 5.03 mmol) in a (1:1) mixed solvent system of 1,4-dioxane:water (105 mL), were added sulfamic acid (2.93 g, 30.15 mmol), sodium chlorite (0.591 g, 6.53 mmol) and potassium dihydrogen phosphate (8.20 g, 60.3 mmol). The mixture was stirred overnight at room temperature The resulting mixture was diluted with water (50 mL) and extracted with ethyl acetate (150 mL×3). The combined organic phases were washed with brine, dried and concentrated in vacuo to a yellow solid which was thoroughly washed with hexane to give 2-bromo-3-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1.62 g, 79%) as off-white solid. LC-MS: 406.2 (M−H).

Workup

  1. extractionextracted with ethyl acetate (150 mL×3)
  2. washThe combined organic phases were washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo to a yellow solid which
  5. washwas thoroughly washed with hexane

Sources & evidence

ORD record
ord-0826aff90914499094ffe484533a9653
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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