Hydrochloric Acid → HCID 178480792, compound

HRID 577683Notes

Reaction equation

HRID 577683 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:13]2[C:14]3[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:15]=3[N:16]=[C:17]([NH:19][C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[N:18]=2)[CH2:9]1)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:9][C@H:10]([NH:12][C:13]2[C:14]3[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:15]=3[N:16]=[C:17]([NH:19][C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[N:18]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178480793HCID 178480793, compound

Product 1

HCID 178480792HCID 178480792, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl((trans)-3-((2-((1-methyl-1H-pyrazol-4-yl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclobutyl)carbamate (115 mg, 0.218 mmol) in DCM (5 mL) was added 4 N HCl in 1,4-dioxane (0.3 mL, 1.2 mmol). The reaction was allowed to stir at rt for 3.5 hrs and then quenched with saturated aqueous NaHCO3 (2 mL). DCM (10 mL) was added and the DCM extract was dried over MgSO4, filtered and concentrated to afford the title compound (87 mg, 93% yield) as a tan foam.

Workup

  1. customquenched with saturated aqueous NaHCO3 (2 mL)
  2. additionDCM (10 mL) was added
  3. extractionthe DCM extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-617c869809a7438bacd96110859e148f
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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