Trifluoroacetic acid → HCID 9805331, compound

HRID 2055643Notes

Reaction equation

HRID 2055643 reaction equation
C(OC(=O)NCCCNC(C1N(CC2C=CC=CC=2)C(=O)C2C=CC=NC=2N=1)C(C)C)(C)(C)C.CCN(C(C)C)C(C)C.C1(C)C=CC(C(Cl)=O)=CC=1.C(OC(=O)[NH:60][CH2:61][CH2:62][CH2:63][N:64]([CH:74]([C:78]1[N:79]([CH2:89][C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C:80](=[O:88])[C:81]2[CH:87]=[CH:86][CH:85]=[N:84][C:82]=2[N:83]=1)[CH:75]([CH3:77])[CH3:76])[C:65](=[O:73])[C:66]1[CH:71]=[CH:70][C:69]([CH3:72])=[CH:68][CH:67]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:60][CH2:61][CH2:62][CH2:63][N:64]([CH:74]([C:78]1[N:79]([CH2:89][C:90]2[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=2)[C:80](=[O:88])[C:81]2[CH:87]=[CH:86][CH:85]=[N:84][C:82]=2[N:83]=1)[CH:75]([CH3:76])[CH3:77])[C:65](=[O:73])[C:66]1[CH:71]=[CH:70][C:69]([CH3:72])=[CH:68][CH:67]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 134054-Methylbenzoyl ChlorideHCID 81531DiisopropylethylamineHCID 69316069HCID 69316069, compoundHCID 131725729HCID 131725729, compound

Product 1

HCID 9805331HCID 9805331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a mixture of N-{3-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-2-methyl-proplyamino]-propyl}-carbamic acid tert butyl ester (110 mg, 0.236 mmol), DIEA (82 μL, 0.473 mmol) and dichloromethane (2 mL) was added p-toluoyl chloride (47 μL, 0.354 mmol) dropwise. The reaction mixture was stirred at room temperature overnight, and then diluted with dichloromethane and washed with saturated sodium bicarbonate, water and brine. After concentration, the residue was subjected to flash silica gel chromatography using hexane-EtOAc (1:2) and EtOAc-MeOH (20:1) as eluent to give the corresponding crude acylated product, {3-[[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-2-methyl-propyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester, which was then treated with 30% TFA in dichloromethane (3 mL) for 15 minutes, diluted with dichloromethane, washed with saturated sodium bicarbonate, water, and brine, and dried (Na2SO4). Concentration of the dichloromethane solution gave the title product, N-(3-amino-propyl)-N-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-2-methyl-propyl]-4-methyl-benzamide, as a white solid (89 mg, 78%).

Workup

  1. washwashed with saturated sodium bicarbonate, water and brine
  2. concentrationAfter concentration
  3. customto give the corresponding crude
  4. washwashed with saturated sodium bicarbonate, water, and brine
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-c3863616d03742cc97769943a62be9c5
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

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