Sulfamic Acid → HCID 90040678, compound

HRID 523018Notes

Reaction equation

HRID 523018 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[CH3:8].S(=O)(=O)([OH:24])N.P([O-])(O)(O)=O.[K+].Cl([O-])=O.[Na+]>O.C(OCC)(=O)C.O1CCCC1.C(O)(C)(C)C>[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]([CH3:20])([CH3:19])[CH3:21])[C:5]2=[N:6][C:7]=1[CH3:8]

Participants

9

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 90040927HCID 90040927, compound

Product 1

HCID 90040678HCID 90040678, compoundYield 91.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 2-bromo-3-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (3.17 g, 8.55 mmol), tert-butanol (10 mL), tetrahydrofuran (10 mL), and water (10 mL) was added sulfamic acid (3.32 g, 34 mmol) and then a solution of potassium dihydrogen phosphate (8.85 g, 65 mmol) and sodium chlorite (1.93 g, 21 mmol) in water (42 mL). After 1 h the mixture was diluted with ethyl acetate, washed once with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 2-bromo-3-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3.02 g, 91%) as a light yellow solid. This material was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.10 (s, 9H), 0.83 (t, J=8.0 Hz, 2H), 2.69 (s, 3H), 3.55 (t, J=8.0 Hz, 2H), 5.64 (s, 2H), 8.64 (s, 1H), 12.46 (br s, J=9.06 Hz, 1H, —COOH).

Workup

  1. washwashed once with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4607672a75de468493477682530425c9
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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