Sulfamic Acid → HCID 67386109, compound

HRID 1898637Notes

Reaction equation

HRID 1898637 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:9]1[CH:13]=[C:12]([C:14]2[N:15]=[C:16]3[C:22]([CH:23]=[O:24])=[CH:21][N:20]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:17]3=[N:18][CH:19]=2)[N:11]=[CH:10]1.S(=O)(=O)([OH:35])N.Cl([O-])=O.[Na+].OP([O-])(O)=O.[K+]>O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:9]1[CH:13]=[C:12]([C:14]2[N:15]=[C:16]3[C:22]([C:23]([OH:35])=[O:24])=[CH:21][N:20]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:17]3=[N:18][CH:19]=2)[N:11]=[CH:10]1

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86657875HCID 86657875, compound

Product 1

HCID 67386109HCID 67386109, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-[1-(2,5-difluoro-phenyl)-1H-imidazol-4-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (0.087 g, 0.19 mmol) and sulfamic acid (0.127 g, 1.30 mmol) in 2 mL of 1,4-dioxane and 0.2 mL of water was treated dropwise with a mixture of sodium chlorite (0.031 g, 0.27 mmol) and KH2PO4 (0.335 g, 2.46 mmol)) in 1 mL of water, rinsing with 1 mL of water. The pale yellow solution was stirred 1.25 h as a white precipitate formed. The mixture was partitioned between 10 mL of water and 10 mL of ethyl acetate. The organic layer was washed with 10 mL of a sat. aq. NaCl solution, dried over Na2SO4, filtered and concentrated to afford 0.067 g (74%) of 2-[1-(2,5-difluoro-phenyl)-1H-imidazol-4-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a pale yellow solid, which was used without further purification. MS: (M+H)+=472.

Workup

  1. washrinsing with 1 mL of water
  2. customformed
  3. customThe mixture was partitioned between 10 mL of water and 10 mL of ethyl acetate
  4. washThe organic layer was washed with 10 mL of a sat. aq. NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dea1ccea242b4c1690dbf3b5a5522836
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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