Tert-butyldicarbonate → HCID 135510703, compound

HRID 641766Notes

Reaction equation

HRID 641766 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:26])=[CH:16][C:17]=3[O:19][CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:27][CH2:28][O:29][C:5]2=[CH:4][CH:3]=1.[C:30](OC([O-])=O)([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C=O)C>[C:33]([O:32][C:30]([N:23]1[CH2:22][CH2:21][CH:20]([O:19][C:17]2[CH:16]=[C:15]([OH:26])[CH:14]=[C:13]3[C:18]=2[C:9]([NH:8][C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]4[O:29][CH2:28][O:27][C:6]=24)=[N:10][CH:11]=[N:12]3)[CH2:25][CH2:24]1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 22064466Tert-butyldicarbonateHCID 135510683HCID 135510683, compound

Product 1

HCID 135510703HCID 135510703, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-5-piperidin-4-yloxyquinazoline (1.4 g), di-(tert-butyl dicarbonate (0.737 g) and DMF (14 ml) was stirred at ambient temperature for 2 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 24:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (1.2 g); NMR Spectrum: (CDCl3) 1.5 (s, 9H), 1.7-1.9 (m, 2H), 2.0-2.15 (m, 2H), 3.0-3.15 (m, 2H), 3.8-3.95 (m, 2H), 4.6 (m, 1H), 6.02 (s, 2H), 6.55 (s, 1H), 6.72 (d, 1H), 6.98 (m, 2H), 8.4 (s, 1H), 9.4 (s, 1H); Mass Spectrum: M+H+ 515 and 517.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica using
  7. additiona 24:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-acce2966284246baba42ca1575b4aef1
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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