Dichloromethane → HCID 60209264, compound

HRID 2374042Notes

Reaction equation

HRID 2374042 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:8]=2)=[C:4]([F:22])[CH:3]=1.COC1C=CC(CNC2N=CN=C(OC3C=CC(N[C:45]([NH:47][C:48](=[O:57])[CH2:49][C:50]4[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=4)=[O:46])=CC=3F)C=2)=CC=1.C(Cl)[Cl:62]>>[ClH:62].[CH3:19][N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][NH:13][C:9]1[CH:8]=[C:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([NH:1][C:45]([NH:47][C:48](=[O:57])[CH2:49][C:50]3[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=3)=[O:46])=[CH:3][C:4]=2[F:22])[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 115698931-(4-(6-(4-Methoxybenzylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea2×HCID 59852916N3-[4-[(4-Amino-2-fluorophenyl)methyl]-2-pyridinyl]-N1,N1-dimethyl-1,3-propanediamine

Product 1

HCID 60209264HCID 60209264, compoundYield 14%

Procedure

To a solution of 4-(4-amino-2-fluorobenzyl)-N-(3-(dimethylamino)propyl)pyridin-2-amine (30 mg, 0.1 mmol) in DCM (2 mL) was added a solution of 2-(4-fluorophenyl)acetyl isocyanate (Compound D of Example 11, 0.347 M in toluene, 0.25 mL). The mixture was stirred at room temperature for 0.5 h before it was quenched with MeOH. The solution was concentrated in vacuo and the residue was purified by prep. HPLC. The desired fractions were collected and concentrated in vacuo. The residue was dissolved in MeOH and polymer bound diethylene triamine (50 mg) was added to remove trifluoroacetic acid. After filtration and concentration, the residue was converted to a hydrochloride salt by the addition of 1 N HCl (0.5 mL) and lyophilized to give 1-(4-((2-(3-(dimethylamino)propylamino)pyridin-4-yl)methyl)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea hydrochloride (8.0 mg, 14% yield). MS(ESI+): m/z 482.24 (M+H)+.

Workup

  1. customwas quenched with MeOH
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was purified by prep
  4. customThe desired fractions were collected
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in MeOH
  7. additionpolymer bound diethylene triamine (50 mg) was added
  8. customto remove trifluoroacetic acid
  9. filtrationAfter filtration and concentration
  10. additionthe residue was converted to a hydrochloride salt by the addition of 1 N HCl (0.5 mL)

Sources & evidence

ORD record
ord-9e28a2e04f15467393467522310f5c3e
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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