4-Methylmorpholine → HCID 178471566, compound

HRID 1494615

Reaction equation

HRID 1494615 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:27])[C:8]2[CH:14]=[C:13]([CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=3)C)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].[CH3:28]N1CCOCC1.C1(NP(Cl)(=O)OC2C=CC=CC=2)C=CC=CC=1.[NH2:52][C@H:53]([C:61]([O:63][CH2:64][CH3:65])=[O:62])[CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57]>CN1CCCC1=O>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:27])[C:8]2[CH:14]=[C:13]([C:15]([CH3:28])=[CH:16][C:18]3[CH:23]=[CH:22][C:21]([C:24]([NH:52][C@H:53]([C:61]([O:63][CH2:64][CH3:65])=[O:62])[CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57])=[O:25])=[CH:20][CH:19]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 73961Glutamic acid diethyl esterHCID 103959Phosphoramidochloridic acid, N-phenyl-, phenyl esterHCID 178474469HCID 178474469, compound

Product 1

HCID 178471566HCID 178471566, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 0.2 g of 2-acetamido-4-hydroxy-6-[2-(4-carboxyphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine in 50 mL of N-methylpyrrolidinone containing 0.18 g of N-methylmorpholine was added 0.22 g of phenyl N-phenylphosphoramidochloridate in a single portion. After stirring the mixture at room temperature for 1 hour, 0.20 g of diethyl L-glutamate was added. The reaction mixture was stirred overnight, the solvent was removed under reduced pressure and the residue was triturated with chloroform. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was subjected to preparative thin layer chromatography on silica gel using a 5% methanol in chloroform mixture as the eluent. This gave 74.6 mg (25%) of the title compound as a pale yellowish solid; NMR (CDCl3, 250 MHz) d 1.22(t, 3H, J=7.1 Hz), 1.30(t, 3H J=7.1 Hz), 2.11-2.57(m, 10H), 4.14(q, 2H, J=7.1 Hz), 4.24(q, 2H, J=7.1 Hz), 4.75-4.83(m, 1H), 6.86(brs, 1H), 7.18(brs, 1H), 7.57(d, 2H, J= 8.42 Hz), 7.84(d, 2H, J=8.42 Hz), 8.50(d, 1H, J=2.01 Hz), 8.96(brs, 1H), 10.34(brs, 1H).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was triturated with chloroform
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fee372889e0f4429a59d33b98a5e9e9b
Source dataset
uspto-grants-1991_06
Patent number
US05026851

Linked notes

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