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

HRID 1766085Notes

Reaction equation

HRID 1766085 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 l). 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-02e66af561214002ae8e731c3cf423ad
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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