Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 49823095, compound

HRID 2114811Notes

Reaction equation

HRID 2114811 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:15]([OH:17])=O.FC(F)(F)C(O)=O.[CH2:29]([O:36][C:37](=[O:49])[N:38]=[C:39]([NH2:48])[N:40]1[CH2:45][CH2:44][CH:43]([CH2:46][NH2:47])[CH2:42][CH2:41]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:29]([O:36][C:37](=[O:49])[N:38]=[C:39]([NH2:48])[N:40]1[CH2:41][CH2:42][CH:43]([CH2:46][NH:47][C:15](=[O:17])[C:14]2[CH:18]=[CH:19][C:20]([CH3:21])=[C:12]([O:11][CH2:10][CH2:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH:13]=2)[CH2:44][CH2:45]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220523883-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methyl-benzoic acidHCID 69305786HCID 69305786, compound

Product 1

HCID 49823095HCID 49823095, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

97 mg of 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methyl-benzoic acid and 124.3 mg of [Amino-(4-aminomethyl-piperidin-1-yl)-methylene]-carbamic acid benzyl ester trifluoroacetic acid salt were dissolved in 5 ml of DMF. After cooling to 0° C. 136 mg of HATU and 106 mg of NEM were added. The mixture was stirred at 0° C. for 2 hours and at room temperature for 3 hours. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC (C18 reverse phase column) (gradient acetonitrile water (containing 0.1% trifluoro-acetic acid) 90:10 to 0:100). The fractions containing the product were evaporated and lyophilized.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC (C18 reverse phase column) (gradient acetonitrile water (containing 0.1% trifluoro-acetic acid) 90:10 to 0:100)
  3. additionThe fractions containing the product
  4. customwere evaporated

Sources & evidence

ORD record
ord-3e8d86efac234ab98b1d5d7e55df7140
Source dataset
uspto-grants-2008_10
Patent number
US07435747B2

Reaction notes

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