Sodium hydride → HCID 68227620, compound

HRID 1400165Notes

Reaction equation

HRID 1400165 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:8]=2)[N:3]=1.Br[CH2:30][CH:31]([CH2:39]Br)[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:39][C:31](=[CH2:30])[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13347324tert-butyl 3-bromo-2-(bromomethyl)propanoateHCID 52919528HCID 52919528, compound

Product 1

HCID 68227620HCID 68227620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of ethyl 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]acetate are suspended in 10 ml of DMF, and 1 g of tert-butyl 3-bromo-2-(bromomethyl)propanoate is added. 324 mg of sodium hydride are subsequently added with ice-cooling, and the mixture is stirred with cooling for a further 30 min. After 1 h at 23° C., the mixture is poured into 50 ml of saturated ammonium chloride solution, with a precipitate forming. This is filtered off, washed with water and dried at 50° C. for 12 h. Yield: 900 mg (66%) of O1-tert-butyl O5-ethyl 4-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-2-methylenepentanedioate;

Workup

  1. temperaturecooling
  2. temperaturewith cooling for a further 30 min
  3. customforming
  4. filtrationThis is filtered off
  5. washwashed with water
  6. customdried at 50° C. for 12 h

Sources & evidence

ORD record
ord-971d013ee3e444ae8ca6fc19c1fce4c8
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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