Putrescine → HCID 10111301, compound

HRID 1393135Notes

Reaction equation

HRID 1393135 reaction equation
Cl.[NH2:2][C:3]1[N:12]=[C:11]([NH2:13])[C:10]2[C:5](=[N:6][CH:7]=[C:8]([CH2:14][N:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=3)[CH3:16])[N:9]=2)[N:4]=1.NC1N=C(N)C2C(=NC=C(CN(C3C=CC(C(O)=O)=CC=3)C)N=2)N=1.C(N(CC)C(C)C)(C)C.C(P(=O)(OCC)OCC)#N.[NH2:69][CH2:70][CH2:71][CH2:72][CH2:73][NH2:74].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:69][CH2:70][CH2:71][CH2:72][CH2:73][NH:74][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([N:15]([CH2:14][C:8]2[N:9]=[C:10]3[C:5](=[N:6][CH:7]=2)[N:4]=[C:3]([NH2:2])[N:12]=[C:11]3[NH2:13])[CH3:16])=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 1045PutrescineHCID 76257Diethyl cyanophosphonateHCID 81531Diisopropylethylamine2×HCID 516892Sodium BicarbonateHCID 66957731Methotrexate Related Compound E (50 mg) (4-{[(2,4-Diaminopteridin-6-yl)methyl](methyl)amino}benzoic acid, hemihydrochloride)

Product 1

HCID 10111301HCID 10111301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-[N-(2,4-diamino-6-pteridinylmethyl)-N-methylamino]benzoic acid hemihydrochloride (250 mg, 0.73 mmol) in dry DMF (20 ml) were added N,N-diisopropylethylamine (250 μl, 1.46 mmol, 2 equiv) and diethyl cyanophosphonate (225 μl, 1.46 mmol, 2 equiv). Dissolution occurred rapidly and the reaction was stirred for 4 hours at room temperature. 1,4-Diaminobutane (367 μl, 3.65 mmol, 5 equiv) and N,N-diisopropylethylamine (250 μl, 1.46 mmol, 2 equiv) were then added and the solution was stirred 45 minutes at room temperature. The completion of reaction was verified by HPLC, and solid NaHCO3 was added. The solvent was then evaporated under reduced pressure and the residue suspended in a small amount of methanol. Addition of dilute aqueous NH4OH was then followed by filtration and a rinse with water gave the product upon drying to yield 153 mg (53%): MS m/z (M+H) 396, HPLC Rt=3.80 min.

Workup

  1. dissolutionDissolution
  2. stirringthe solution was stirred 45 minutes at room temperature
  3. customThe completion of reaction
  4. additionwas added
  5. customThe solvent was then evaporated under reduced pressure
  6. additionAddition of dilute aqueous NH4OH
  7. filtrationwas then followed by filtration
  8. washa rinse with water
  9. customgave the product
  10. customupon drying
  11. customto yield 153 mg (53%)

Sources & evidence

ORD record
ord-7b70ff60261048118903bf930b4e0884
Source dataset
uspto-grants-2008_03
Patent number
US07345048B2

Reaction notes

Loading…