Butanethiol → HCID 25061237, compound

HRID 2244061Notes

Reaction equation

HRID 2244061 reaction equation
[CH2:1]([SH:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([N:20]3[C:28]4[CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][C:24](=[O:31])[C:23]=4[C:22]([CH3:32])=[CH:21]3)=[CH:16][C:17]=2F)[N:12]=[CH:11][N:10]=1>CN(C=O)C>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([N:20]3[C:28]4[CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][C:24](=[O:31])[C:23]=4[C:22]([CH3:32])=[CH:21]3)=[CH:16][C:17]=2[S:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 8012ButanethiolHCID 24758Sodium hydrideHCID 250612361-(4-Amino-5-fluoro-7-quinazolinyl)-1,5,6,7-tetrahydro-3,6,6-trimethyl-4H-indol-4-one

Product 1

HCID 25061237HCID 25061237, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a small microwave vial with a stir bar, butanethiol (0.494 mmol, 44.56 mg) is dissolved in 3 mL DMF. To this solution is added NaH (60% suspension in mineral oil) (0.494 mmol, 20 mg) and the mixture is stirred at rt for 5 minutes and then 1-(4-Amino-5-fluoro-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.0988 mmol, 33.4 mg) is added. The reaction is sealed and placed in the microwave reactor where it is heated to 120° C. for 30 min. The reaction is cooled and quenched by pouring into 30 ml sat. NH4Cl aq. and extracted 3 times with 10 mL EtOAc. The combined organics are dried with Na2SO4, concentrated, and purified by silica gel chromatography on Biotage using a gradient of 0-20% MeOH in DCM. 1-(4-Amino-5-butylsulfanyl-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one is isolated (22.1 mg, LC/MS m/z=409 [M+H]+) as a yellow powder.

Workup

  1. customThe reaction is sealed
  2. temperatureis heated to 120° C. for 30 min
  3. temperatureThe reaction is cooled
  4. customquenched
  5. additionby pouring into 30 ml sat. NH4Cl aq.
  6. extractionextracted 3 times with 10 mL EtOAc
  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-23b5919b9e4e4b6b8f5e3056fcad3332
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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