Hydrochloric Acid → HCID 46869311, compound

HRID 578661Notes

Reaction equation

HRID 578661 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH:10]([NH:17][C:18]1[C:27]2[C:22](=[C:23]([C:30](=[O:32])[NH2:31])[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C)(C)(C)C.C1COCC1.Cl>O1CCOCC1>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[C:23]([C:30]([NH2:31])=[O:32])[CH:24]=1)[N:21]=[CH:20][N:19]=[C:18]2[NH:17][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][NH:7][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 66763960HCID 66763960, compound

Product 1

HCID 46869311HCID 46869311, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A scintillation vial equipped with a stir bar was charged with [2-(8-carbamoyl-6-methoxy-quinazolin-4-ylamino)-2-phenyl-ethyl]-methyl-carbamic acid tert-butyl ester (150 mg, 0.33 mmol) and THF, (5 mL). Then, 4 M HCl in dioxane, (5 mL) was added at RT and the mixture was stirred overnight. After 18 h, a white precipitate had formed and LCMS indicated consumption of SM. The mixture was diluted with Et2O (30 mL) and the precipitate was filtered through a filter paper and washed with Et2O, (30 mL). The solid was dried under vacuum. Amount obtained: 114 mg, 0.32 mmol, 100% yield. LCMS (ESI) 352 (M+H).

Workup

  1. customA scintillation vial equipped with a stir bar
  2. waitAfter 18 h
  3. customa white precipitate had formed
  4. customconsumption of SM
  5. additionThe mixture was diluted with Et2O (30 mL)
  6. filtrationthe precipitate was filtered through a filter paper
  7. washwashed with Et2O, (30 mL)
  8. customThe solid was dried under vacuum
  9. customAmount obtained

Sources & evidence

ORD record
ord-02405b523e8b41ae8bef692288214109
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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