Hydrochloric Acid → HCID 46869029, compound

HRID 578664Notes

Reaction equation

HRID 578664 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH:10]([NH:18][C:19]1[C:28]2[C:23](=[C:24]([C:37](=[O:39])[NH2:38])[CH:25]=[C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:27]=2)[N:22]=[CH:21][N:20]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)C)(C)(C)C.C1COCC1.Cl>O1CCOCC1>[CH2:30]([O:29][C:26]1[CH:27]=[C:28]2[C:23](=[C:24]([C:37]([NH2:38])=[O:39])[CH:25]=1)[N:22]=[CH:21][N:20]=[C:19]2[NH:18][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:9][NH:7][CH3:6])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 66763625HCID 66763625, compound

Product 1

HCID 46869029HCID 46869029, compoundYield 97%

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-(3-chloro-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (20 mg, 0.035 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: 15 mg, 0.034 mmol, 97% yield. LCMS (ESI) 462 (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-c3d7ae2f62ba49d9ae0d5306a06e0705
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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