Sulfamic Acid → 2-(1-((1-(tert-Butoxycarbonyl)azetidin-3-yl)methyl)-6-fluoro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 246526Notes

Reaction equation

HRID 246526 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:23]3[N:24]=[C:25]4[C:31]([CH:32]=[O:33])=[CH:30][N:29]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:26]4=[N:27][CH:28]=3)=[N:7][N:8]2[CH2:11][CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)=[CH:4][CH:3]=1.S(=O)(=O)([OH:44])N.Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[K+]>O1CCOCC1.O>[C:19]([O:18][C:16]([N:14]1[CH2:13][CH:12]([CH2:11][N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=3)[C:6]([C:23]3[N:24]=[C:25]4[C:31]([C:32]([OH:44])=[O:33])=[CH:30][N:29]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:26]4=[N:27][CH:28]=3)=[N:7]2)[CH2:15]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86677984tert-butyl 3-((6-fluoro-3-(7-formyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate

Product 1

HCID 712801702-(1-((1-(tert-Butoxycarbonyl)azetidin-3-yl)methyl)-6-fluoro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 3-((6-fluoro-3-(7-formyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate (160 mg, 276 μmol) and sulfamic acid (161 mg, 1.65 mmol) in dioxane (5 mL) and water (2 mL), cooled to 0° C., was added a solution of sodium chlorite (32.4 mg, 358 μmol) and potassium dihydrogen phosphate (450 mg, 3.31 mmol) in water (3 mL) dropwise. The mixture was warmed to room temperature. After 2.5 h, the mixture was partitioned between ethyl acetate and water and the organic phase separated and washed with water then dried and concentrated in vacuo. A quantitative yield was assumed and the crude residue used directly in the next step without further purification.

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. customthe organic phase separated
  3. washwashed with water
  4. customthen dried
  5. concentrationconcentrated in vacuo
  6. customthe crude residue used directly in the next step without further purification

Sources & evidence

ORD record
ord-fc20b63ae500462e909e01a82183861c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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