Acetic Acid → HCID 137199429, compound

HRID 628303Notes

Reaction equation

HRID 628303 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:19](S(C2C=CC=CC=2)(=O)=O)[C:18]2[C:13](=[N:14][C:15]([N:29](C(OC(C)(C)C)=O)[NH:30][C:31](OC(C)(C)C)=O)=[CH:16][CH:17]=2)[CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].[NH4+].[Cl-].[CH3:49]C(O)=O>>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[NH:19][C:18]2[CH:17]=[CH:16][C:15]3[N:14]([C:31]([CH3:49])=[N:30][N:29]=3)[C:13]=2[CH:12]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 123326231HCID 123326231, compound

Product 1

HCID 137199429HCID 137199429, compound

Conditions

Temperature
180 °C

Procedure

di-tert-Butyl 1-[2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (4.9 g, 7.6 mmol, from Step 2) in AcOH (60 mL) was divided into portions and each was heated in the microwave to a temperature of 180° C. for 4 minutes. The portions were combined and AcOH was removed in vacuo and the residue was dissolved in tetrahydrofuran (61 mL) and methanol (61 mL) and cooled to 0° C. 2.8 M NaOH (70 mL, 200 mmol) was added. After stirring for 15 minutes, sat′d NH4Cl was added and the product was extracted with DCM. The combined extracts were dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as an off-white solid (1.2 g, 48%).

Workup

  1. customAcOH was removed in vacuo
  2. dissolutionthe residue was dissolved in tetrahydrofuran (61 mL)
  3. temperaturemethanol (61 mL) and cooled to 0° C
  4. additionwas added
  5. extractionthe product was extracted with DCM
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as an off-white solid (1.2 g, 48%)

Sources & evidence

ORD record
ord-0011712193f9400fbd42633c54a2c696
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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