Sulfuric Acid → HCID 178482082, compound

HRID 527939Notes

Reaction equation

HRID 527939 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:24])[C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[N:17]=3)[CH2:11]2)=[N:3][CH:2]=1.S(=O)(=O)(O)O.[N:30]([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:24])[C:16]3[N:17]=[C:18]4[NH:23][N:30]=[N:22][C:19]4=[CH:20][CH:21]=3)[CH2:11]2)=[N:3][CH:2]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 68027261HCID 68027261, compound

Product 1

HCID 178482082HCID 178482082, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (R)—N2-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-N2-methylpyridine-2,5,6-triamine (50 mg, 0.15 mmol,) in water (0.6 mL) was added concentrated sulfuric acid (23 uL). The mixture was stirred at room temperature for 1 h. It was cooled to 0° C. and aqueous sodium nitrite (17 mg, 0.25 mmol, in 0.1 mL of water) was added. The reaction mixture was stirred at 0° C. for 1 h. It was then neutralized till pH equal to 5 with aqueous NaHCO3 (10%) and extracted with EtOAc (3×10 mL). The combined extracts were washed with brine (2×10 mL), concentrated, and the residue was purified by chromatography to give the title compound. MS (m/z): 336 (M+H)+.

Workup

  1. temperatureIt was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 1 h
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined extracts were washed with brine (2×10 mL)
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-d3847419369744209aae1df108092a69
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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