Sodium hydride → HCID 25060728, compound

HRID 2244053Notes

Reaction equation

HRID 2244053 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].F[C:17]1[CH:26]=[C:25]2[C:20]([C:21]([NH2:28])=[N:22][C:23]([NH2:27])=[N:24]2)=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[NH2:27][C:23]1[N:22]=[C:21]([NH2:28])[C:20]2[C:25](=[CH:26][C:17]([N:4]3[C:5]4[CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8][C:9](=[O:11])[C:10]=4[C:2]([CH3:1])=[CH:3]3)=[CH:18][CH:19]=2)[N:24]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 4562212,4-Quinazolinediamine, 7-fluoro-HCID 516892Sodium BicarbonateHCID 248207983,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one

Product 1

HCID 25060728HCID 25060728, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To 3,6,6,-trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.41 g, 1.2 eq) in dimethylacetamide (50 mL) is added slowly sodium hydride (69.5 mg, 1.5 eq) and the resulting mixture is stirred at RT for 0.5 h. Then 7-Fluoro-quinazolin-2,4-diamine (0.342 g, 1 eq) is added and the mixture is stirred at 150° C. for overnight. The reaction mixture is poured into sat'd NaHCO3 aq. solution (300 mL), extracted by EtOAc (3×150 mL). The combined organic layers are dried over Na2SO4, filtered, concentrated. The crude product is purified by flash chromatography to give 1-(2,4-Diamino-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.5 g, 77.6% yield). LC/MS m/z=336 [M+H]+.

Workup

  1. stirringthe mixture is stirred at 150° C. for overnight
  2. extractionextracted by EtOAc (3×150 mL)
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-d41c172ba27049b7b69bd6efd3321997
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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