4-Methylmorpholine → HCID 5328967, compound

HRID 1069005Notes

Reaction equation

HRID 1069005 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]#[C:7][C:8]([OH:10])=O.ClC(OCC(C)C)=O.CN1CCOCC1.[Br:26][C:27]1[CH:28]=[C:29]([NH:33][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[C:41]([NH2:44])[CH:42]=3)[N:37]=[CH:36][N:35]=2)[CH:30]=[CH:31][CH:32]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:26][C:27]1[CH:28]=[C:29]([NH:33][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[C:41]([NH:44][C:8](=[O:10])[C:7]#[C:6][CH2:5][O:4][CH2:3][O:2][CH3:1])[CH:42]=3)[N:37]=[CH:36][N:35]=2)[CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamineHCID 10942555HCID 10942555, compound

Product 1

HCID 5328967HCID 5328967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.66 g of 4-methoxymethoxy-but-2-ynoic acid and 0.60 mL of isobutyl chloroformate in 16 mL of tetrahydrofuran at 0° C. was added 0.5 mL of N-methylmorpholine followed by 1.2 g of solid N-(3-bromophenyl)-4,6-quinazolindiamine. Stirring was continued for 1 hr at 0° C. and 30 min at room temperature. Another equal amount of mixed anhydride as prepared above was added. The mixture was stirred an addition 30 min and stored at −10° C. over night. The mixture was poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organic solution was dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel eluting with ethyl acetate and choroform solvent mixtures to give 0.35 g of 4-Methoxymethoxy-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide as a tan solid: mass spectrum (m/e): M+H 441.0.

Workup

  1. additionabove was added
  2. stirringThe mixture was stirred
  3. additionan addition 30 min
  4. waitstored at −10° C. over night
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic solution was dried over magnesium sulfate
  7. customThe solvent was removed
  8. customthe residue was chromatographed on silica gel eluting with ethyl acetate and choroform solvent mixtures

Sources & evidence

ORD record
ord-bb383e02f4e143ffa90749df7bbd1a0f
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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