Hydrochloric Acid → HCID 68227263, compound

HRID 1400164Notes

Reaction equation

HRID 1400164 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(OCC)=O)[CH:8]=2)[N:3]=1.Br[CH2:30][CH2:31][CH2:32][CH2:33]Br.[H-].[Na+].[OH-:37].[Na+].Cl.CN([CH:43]=[O:44])C>>[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]([CH:23]3[CH2:33][CH2:32][CH2:31][CH:30]3[C:43]([OH:44])=[O:37])[CH:8]=2)[N:3]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 24758Sodium hydride2×HCID 52919528HCID 52919528, compound

Product 1

HCID 68227263HCID 68227263, compound

Conditions

Temperature
23 °C

Procedure

188 mg of ethyl 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]acetate are suspended in 1 ml of DMF, and 60 μl of 1,4-dibromobutane are added. 80 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 re-cooled, and a further 10 mg of sodium hydride are added to the mixture. The mixture is stirred at 23° C. for a further 30 min, 1 ml of 2N sodium hydroxide solution is added, and the mixture is stirred at 70° C. for 12 h. After cooling to 23° C., the mixture is acidified by dropwise addition of 1N hydrochloric acid, with a yellow precipitate forming. This is filtered off, washed with water and dried at 50° C. for 12 h.

Workup

  1. temperaturecooling
  2. temperaturewith cooling for a further 30 min
  3. temperaturethe mixture is re-cooled
  4. stirringThe mixture is stirred at 23° C. for a further 30 min
  5. stirringthe mixture is stirred at 70° C. for 12 h
  6. customforming
  7. filtrationThis is filtered off
  8. washwashed with water
  9. customdried at 50° C. for 12 h.

Sources & evidence

ORD record
ord-516e0415e4c04692bf0011aef6d73e42
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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