Sulfuric Acid → HCID 24938251, compound

HRID 422112Notes

Reaction equation

HRID 422112 reaction equation
[F:1][C:2]1[C:3]([C:17]2[S:21][C:20]3[C:22]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][C:27]=4[NH:32]C(=O)C(C)(C)C)=[CH:23][CH:24]=[CH:25][C:19]=3[CH:18]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[N:6][CH:7]=1.OS(O)(=O)=O>O>[NH2:32][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:26]=1[C:22]1[C:20]2[S:21][C:17]([C:3]3[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][CH2:9][CH2:10][N:11]4[CH2:15][CH2:14][NH:13][C:12]4=[O:16])[N:4]=3)=[CH:18][C:19]=2[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 66674686HCID 66674686, compound

Product 1

HCID 24938251HCID 24938251, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Transfer the amide intermediate to a 40 mL septum capped vial. Add a magnetic stir bar and charge water (20 mL) and concentrated H2SO4 (5 mL) to the vial. Warm the vial to 90° C. in an oil bath for 5 hours. Cool the reaction to room temperature and pass through an SCX (10 g) column. Elute with water/methanol 1:1, then 100% methanol, then 1:1 dichloromethane/methanol, and finally elute the product off with 10% 2 M ammonia in methanol/90% dichloromethane. Concentrate in vacuo. Chromatograph on silica (80 g) eluting with gradient of 0% to 10% 2 M ammonia/methanol solution in dichloromethane. Dry in vacuum oven at 42° C. for 2 hours to give the title compound (192.6 mg, 48%) as a gold solid. MS (ES) m/z 450 [M+1]+.

Workup

  1. customcapped vial
  2. additionAdd a magnetic stir bar
  3. temperatureCool
  4. customthe reaction to room temperature
  5. washElute with water/methanol 1:1
  6. wash100% methanol, then 1:1 dichloromethane/methanol, and finally elute the product off with 10% 2 M ammonia in methanol/90% dichloromethane
  7. concentrationConcentrate in vacuo
  8. washChromatograph on silica (80 g) eluting with gradient of 0% to 10% 2 M ammonia/methanol solution in dichloromethane
  9. customDry in vacuum oven at 42° C. for 2 hours

Sources & evidence

ORD record
ord-730e2cd1a2214e4fb6c16829b7e32355
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

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