alpha-Methyl-DL-leucine → HCID 178509621, compound

HRID 1678738Notes

Reaction equation

HRID 1678738 reaction equation
[OH:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1.[NH2:29]C(C)(CC(C)C)C(O)=O>CN(C=O)C.O1CCOCC1.Cl>[NH2:29][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([C:9]2[C:8]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:7][C:6]3[C:5]4=[N:4][N:3]=[C:2]([OH:1])[N:14]4[CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 95515alpha-Methyl-DL-leucineHCID 178519435HCID 178519435, compound

Product 1

HCID 178509621HCID 178509621, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 4-(3-hydroxy-9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)-benzaldehyde (3-6, 2.4 g, 6.6 mmol) and 2-amino-2,4-dimethylpentanoic acid (3-7, 1.9 g, 13.1 mmol) in DMF (25 mL) was heated at 150° C. for 20 min. The reaction mixture was cooled, diluted with dioxane (50 mL) and 2N HCl (50 mL) and heated at 100° C. for 30 min. The mixture was cooled and purified via reverse phase HPLC (0-60% acetonitrile/water) to give, upon evaporation of the solvent, the title compound as a yellow solid. HRMS m/z (M+1) Calcd: 368.1506. Found 368.1504.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperatureheated at 100° C. for 30 min
  3. temperatureThe mixture was cooled
  4. custompurified via reverse phase HPLC (0-60% acetonitrile/water)
  5. customto give, upon evaporation of the solvent

Sources & evidence

ORD record
ord-fba23d2a5c7643e488e5f84ccd68abb0
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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