Hydrochloric Acid → tert-Butyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxamide

HRID 1435709Notes

Reaction equation

HRID 1435709 reaction equation
[NH2:1][C:2]1[C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)=[N:5][C:6]([S:15][CH3:16])=[N:7]2.C[N:26](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:47](N)([CH3:50])([CH3:49])[CH3:48].C([O-])(O)=O.[Na+].O.Cl>CN(C=O)C.O1CCOCC1.CCOC(C)=O>[C:47]([C:10]1[CH:9]=[C:8]2[C:3]([C:4]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)=[N:5][C:6]([S:15][CH3:16])=[N:7]2)=[C:2]([NH2:1])[C:11]=1[C:12]([NH2:26])=[O:13])([CH3:50])([CH3:49])[CH3:48]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 6385Tert-ButylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 211090815-Amino-2-methylthio4-(3-methoxyphenyl)-quinazoline-6-carboxylic acid

Product 1

HCID 21109118tert-Butyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a 1.8 M solution of 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxylic acid in DMF (1.8 ml) were added TBTU (173 mg) and tert-butylamine (95 μl). The reaction mixture was stirred for 2 h and then poured into a mixture of EtOAc (25 ml) and saturated aqueous NaHCO3 (50 ml). The organic phase was separated and washed with 0.5 M aqueous HCl (50 ml) and brine (50 ml), followed by drying (MgSO4) and concentration under reduced pressure. The title compound was purified by chromatography on silica gel using hept/EtOAc=1/0 to 2/3 (v/v) as the eluent. The title compound was lyophilized from a mixture of dioxane and water containing 1.5 equiv. of HCl.

Workup

  1. customThe organic phase was separated
  2. washwashed with 0.5 M aqueous HCl (50 ml) and brine (50 ml)
  3. customby drying
  4. concentration(MgSO4) and concentration under reduced pressure
  5. customThe title compound was purified by chromatography on silica gel using hept/EtOAc=1/0 to 2/3 (v/v) as the eluent

Sources & evidence

ORD record
ord-3cc07bab7a5f48b2a957d6117336af8f
Source dataset
uspto-grants-2009_11
Patent number
US07618963B2

Reaction notes

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