Tris(hydroxymethyl)aminomethane → HCID 25004192, compound

HRID 1015384Notes

Reaction equation

HRID 1015384 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CN1CCOCC1.[CH3:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Br.C(O)C(N)(CO)CO>CN(C)C=O>[CH3:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 6992o-Xylyl bromideHCID 79724-MethylmorpholineHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25004192HCID 25004192, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) was shaken for 96 hours at 47° C. in the presence of 3-(Morphonlino)propyl polystyrene sulfonamide (PS-NMM) (160 mg; 0.4 mmol) and o-methylbenzyl bromide (68.5 mg; 0.37 mmol) in 4 mL N,N-dimethylformamide. Tris-(2-aminoethyl)aminomethyl polystyrene (PS-Trisamine) (112 mg; 0.4 mmol) was then added to the mixture and continued to shake for an additional 2 hours. Resins were filtered off and rinsed with methanol. Filtrate was concentrated at reduced pressure, and residue was triturated 1N NaOH with ethanol. Solids were collected by filtration to yield 47.9 mg of title compound. (69% yield).

Workup

  1. filtrationResins were filtered off
  2. washrinsed with methanol
  3. concentrationFiltrate was concentrated at reduced pressure, and residue
  4. customwas triturated 1N NaOH with ethanol
  5. filtrationSolids were collected by filtration

Sources & evidence

ORD record
ord-30e2635706a64ddcaecd8994d9e53ecb
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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