1-Amino-2-propanol → HCID 10202626, compound

HRID 731157Notes

Reaction equation

HRID 731157 reaction equation
[OH:1][CH:2]([CH3:5])[CH2:3][NH2:4].C[C:7]1([CH3:27])[C:11]([C:12]([OH:14])=O)=[CH:10][NH:9][CH:8]1/[CH:15]=[C:16]1\[C:17](=[O:26])[NH:18][C:19]2[C:24]\1=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2.CN(C(O[N:36]1[N:44]=[N:43]C2C=CC=[N:42][C:37]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52]CN(C(C)C)C(C)C>CN(C=O)C.C(Cl)(Cl)Cl>[F:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:26])/[C:16]/2=[CH:15]\[C:8]1[NH:9][C:10]([CH3:52])=[C:11]([C:12]([NH:4][CH2:3][CH:2]([OH:1])[CH2:5][N:44]2[N:43]=[N:42][CH:37]=[N:36]2)=[O:14])[C:7]=1[CH3:27]

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 86588161HCID 86588161, compound

Product 1

HCID 10202626HCID 10202626, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

72 mg of 3-(2-H-tetrazol-2-yl)]-2-hydroxy-1-aminopropane was added to the slurry of 105 mg (0.25 mmol) of 5-[(Z)-(5-fluoro-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-fluoro-1,3-dihydro-2H-indol-2-one (480 mg; 1.6 mmol) with the HATU reagent (570 mg; 1.5 mmol) in the presence of Hunig base (3.0 mol; 0.525 ml) in DMF (5 ml) and isolated in pure form by precipitation with chloroform (5 ml) and drying on high vacuum in 92% yield (579 mg)] 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=106 mg of an orange crystalline solid.

Workup

  1. customprepared
  2. dry with materialdrying on high vacuum in 92% yield (579 mg)] 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-8c755f706f6745d98b1f20dada412046
Source dataset
uspto-grants-2009_09
Patent number
US07582756B2

Reaction notes

Loading…