1-Amino-2-propanol → HCID 10300117, compound

HRID 731159Notes

Reaction equation

HRID 731159 reaction equation
[OH:1][CH:2]([CH3:5])[CH2:3][NH2:4].C[C:7]1([CH3:31])[C:11]([C:12]([OH:14])=O)=[CH:10][NH:9][CH:8]1/[CH:15]=[C:16]1\[C:17](=[O:30])[NH:18][C:19]2[C:24]\1=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2.CN(C(O[N:40]1[N:48]=[N:47]C2C=CC=[N:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56]CN(C(C)C)C(C)C>CN(C=O)C.C(#N)C>[OH:1][CH:2]([CH2:5][N:48]1[N:47]=[N:46][CH:41]=[N:40]1)[CH2:3][NH:4][C:12]([C:11]1[C:7]([CH3:31])=[C:8](/[CH:15]=[C:16]2\[C:17](=[O:30])[NH:18][C:19]3[C:24]\2=[CH:23][C:22]([O:25][C:26]([F:27])([F:29])[F:28])=[CH:21][CH:20]=3)[NH:9][C:10]=1[CH3:56])=[O:14]

Participants

7

Reactant 4

HCID 41-Amino-2-propanolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86588163HCID 86588163, compound

Product 1

HCID 10300117HCID 10300117, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

72 mg of 3-(2-H-tetraazol-2-yl)]-2-hydroxy-1-aminopropane was added to the slurry of 121.5 mg (0.25 mmol) of 5-[(Z)-(5-trifluoromethoxy-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid 1-oxy-7-azabenztriazole ester [prepared by activating (3Z)-3-((3,3-dimethyl-4-carboxy-1-H-pyrrol-2-yl)methylene)-5-trifluoromethoxy-1,3-dihydro-2H-indol-2-one (1.768 g; 4.8 mmol) with the HATU reagent (1.758 g; 4.8 mmol) in the presence of Hunig base (9.0 mmol; 1.58 ml) in DMF (25 ml) and isolated in pure form by evaporation and precipitation with anhydrous acetonitrile and drying on high vacuum in 85.5% yield (1.929 g)] in anhydrous dimethylacetamide (1.5 ml). The mixture was stirred for 30 min and evaporated on highvac. The residue was suspended in a mixture methanol-diethylamine 20:1 (3 ml), allowed to crystallize in the refrigerator (5° C.) for 1 hr, filtered, the precipitate washed with ice-cold methanol and dried on highvac. Y=113 mg of an orange crystalline solid.

Workup

  1. customprepared
  2. dry with materialdrying on high vacuum in 85.5% yield (1.929 g)] in anhydrous dimethylacetamide (1.5 ml)
  3. customevaporated on highvac
  4. customto crystallize in the refrigerator (5° C.) for 1 hr
  5. filtrationfiltered
  6. washthe precipitate washed with ice-cold methanol
  7. customdried on highvac

Sources & evidence

ORD record
ord-a3bdffadbde04f118b781ec549813b4d
Source dataset
uspto-grants-2009_09
Patent number
US07582756B2

Reaction notes

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