Water → methyl 4-{[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]amino}-6-iodoquinazoline-8-carboxylate

HRID 474473

Reaction equation

HRID 474473 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Cl[C:16]1[C:25]2[C:20](=[C:21]([C:27]([O:29][CH3:30])=[O:28])[CH:22]=[C:23]([I:26])[CH:24]=2)[N:19]=[CH:18][N:17]=1.O.[OH-].[Na+]>CC#N>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:2]([NH:1][C:16]2[C:25]3[C:20](=[C:21]([C:27]([O:29][CH3:30])=[O:28])[CH:22]=[C:23]([I:26])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 77231312Methyl 4-chloro-6-iodoquinazoline-8-carboxylate

Product 1

HCID 66763868methyl 4-{[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]amino}-6-iodoquinazoline-8-carboxylateYield 14.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolved tert-butyl (35)-3-aminopiperidine-1-carboxylate (632.11 mg; 3.16 mmol; 1.10 eq.) in MeCN (18.00 ml) and TEA (1.00 ml). Added this mixture to methyl 4-chloro-6-iodoquinazoline-8-carboxylate (1000.00 mg; 2.87 mmol; 1.00 eq.). Stirred reaction at room temperature for 45 hours. LCMS indicated M+1=513 present. Diluted reaction with water and 1N NaOH. Filtered the resulting precipitate. Washed with water and dried to give a yellowish solid (210 mg). Carried material on without further purification. LCMS: M+1=513

Workup

  1. customreaction at room temperature for 45 hours
  2. additionDiluted
  3. filtrationFiltered the resulting precipitate
  4. washWashed with water
  5. customdried

Sources & evidence

ORD record
ord-e86dd1e0306b49829c7fcbea9a8491cb
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Linked notes

Loading…