2-Methoxyethylamine → HCID 25061235, compound

HRID 2244058Notes

Reaction equation

HRID 2244058 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[H-].[Na+].[NH2:8][C:9]1[C:18]2[C:13](=[C:14](F)[C:15]([N:19]3[C:27]4[CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][C:23](=[O:30])[C:22]=4[C:21]([CH3:31])=[CH:20]3)=[CH:16][CH:17]=2)[N:12]=[CH:11][N:10]=1>CN(C=O)C>[NH2:8][C:9]1[C:18]2[C:13](=[C:14]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[C:15]([N:19]3[C:27]4[CH2:26][C:25]([CH3:28])([CH3:29])[CH2:24][C:23](=[O:30])[C:22]=4[C:21]([CH3:31])=[CH:20]3)=[CH:16][CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 24758Sodium hydrideHCID 25060729HCID 25060729, compound

Product 1

HCID 25061235HCID 25061235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a small microwave vial with a stir bar, 2-Methoxy-ethylamine (0.1 mmol, 75 mg) is dissolved in 1 mL DMF. To this solution is added sodium hydride (60% suspension in mineral oil) (0.1 mmol, 4 mg) and the mixture is stirred at rt for 5 min. and then 1-(4-Amino-8-fluoro-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.044 mmol, 15 mg) is added. The reaction is sealed and placed in the microwave reactor where it is heated to 150° C. for 30 min. The reaction is cooled and quenched by pouring into 10 mL of Sat'd. NH4Cl aq. and extracted 3 times with 2 mL CH2Cl2. The combined organics are dried with Na2SO4, concentrated, and purified by silica gel chromatography on Biotage using a gradient of 0-50% MeOH in CH2Cl2. 1-[4-Amino-8-(2-methoxy-ethylamino)-quinazolin-7-yl]-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one is isolated (8 mg, LC/MS m/z=393 [M+H]+) as a tan powder.

Workup

  1. customThe reaction is sealed
  2. temperatureis heated to 150° C. for 30 min
  3. temperatureThe reaction is cooled
  4. customquenched
  5. additionby pouring into 10 mL of Sat'd
  6. extractionNH4Cl aq. and extracted 3 times with 2 mL CH2Cl2
  7. dry with materialThe combined organics are dried with Na2SO4
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography on Biotage

Sources & evidence

ORD record
ord-48715a8f1d784899be4c5597bd379c96
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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