Hydrochloric Acid → HCID 66762907, compound

HRID 578672Notes

Reaction equation

HRID 578672 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:36](=[O:38])[NH2:37])[CH:24]=[C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[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>[CH2:29]([O:28][C:25]1[CH:26]=[C:27]2[C:22](=[C:23]([C:36]([NH2:37])=[O:38])[CH:24]=1)[N:21]=[CH:20][N:19]=[C:18]2[NH:17][CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:7][CH3:6])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 66762399HCID 66762399, compound

Product 1

HCID 66762907HCID 66762907, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A scintillation vial equipped with a stir bar was charged with [2-(6-benzyloxy-8-carbamoyl-quinazolin-4-ylamino)-2-phenyl-ethyl]-methyl-carbamic acid tert-butyl ester (81 mg, 0.15 mmol) and THF, (3 mL). Then, 4 M HCl in dioxane, (3 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: 50 mg, 0.12 mmol, 78% yield. LCMS (ESI) 428 (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-475a02fc766b4f5286ddcd1a3d258cce
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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