Sulfamic Acid → HCID 71279931, compound

HRID 246244Notes

Reaction equation

HRID 246244 reaction equation
S(=O)(=O)(O)N.[Cl:6][C:7]1[CH:34]=[CH:33][C:10]2[N:11]([C:14]3[N:15]=[C:16]4[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]4=[N:18][CH:19]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1.Cl([O-])=[O:36].[Na+].P([O-])(O)(O)=O.[K+]>O.CCOC(C)=O.O1CCOCC1>[Cl:6][C:7]1[CH:34]=[CH:33][C:10]2[N:11]([C:14]3[N:15]=[C:16]4[C:22]([C:23]([OH:36])=[O:24])=[CH:21][N:20]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[C:17]4=[N:18][CH:19]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1

Participants

8

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86677965HCID 86677965, compound

Product 1

HCID 71279931HCID 71279931, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

In a 50 mL round-bottomed flask, sulfamic acid (187 mg, 1.54 mmol) and 2-(5-chloro-benzoimidazol-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (110 mg, 0.26 mmol) were combined with dioxane (6 ml) to give a off-white suspension. The reaction mixture was cooled to 5° C. and a solution of sodium chlorite (30.2 mg, 0.33 mmol) and potassium dihydrogen phosphate (35.0 mg, 0.26 mmol) in water (2 ml) was added dropwise via syringe over 5 min. The reaction warmed to room temperature and stirred for 1 h. The reaction was diluted with EtOAc (25 ml) and washed with 50% brine/water. The aqueous layer was back-extracted with EtOAc (15 mL). The organic layers were combined, washed with brine and dried (MgSO4). Evaporation of the solvent gave 90 mg (79%) of 2-(5-chloro-benzoimidazol-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a solid. (M+H)+=444.

Workup

  1. customto give a off-white suspension
  2. temperatureThe reaction warmed to room temperature
  3. washwashed with 50% brine/water
  4. extractionThe aqueous layer was back-extracted with EtOAc (15 mL)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7f369f21e8c446dfbaf2234f2002ea6c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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