1-Propanol → HCID 58382079, compound

HRID 1628097Notes

Reaction equation

HRID 1628097 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:14]3=[N:15][CH:16]=2)=O)=[CH:5][CH:4]=1.C(O)CC.CC1C=CC(S([NH:44][NH2:45])(=O)=O)=CC=1.N1CCOCC1>O1CCOCC1.Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:44]=[N:45][N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=5)(=[O:21])=[O:22])[C:14]=4[N:15]=[CH:16][C:11]=23)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 10311-PropanolHCID 8083MorpholineHCID 15303P-ToluenesulfonylhydrazideHCID 58382264HCID 58382264, compound

Product 1

HCID 58382079HCID 58382079, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The (4-methoxyphenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanone (2.25 g, 5.52 mmol, prepared using AT from Preparation #AF.1) was dissolved in 1,4-dioxane (25 mL) and PrOH (5 mL) then treated with 4-methylbenzenesulfonohydrazide (1.08 g, 5.80 mmol). The mixture was heated to about 100° C. for about 2 h then it was treated with 1 drop concentrated HCl. The mixture was stirred about 1 h at about 100° C. and then the mixture was concentrated under reduced pressure. The material was dissolved in morpholine (15.0 mL, 172 mmol) then the mixture was heated to about 100° C. for about 15 min. The mixture was cooled to rt and concentrated on the under reduced pressure. The material was treated with water (100 mL) and EtOAc (˜40 mL). The mixture was stirred for about 10 min then filtered. The solids were washed with EtOAc (˜7 mL) then dried to a constant weight under vacuum at about 70° C. to give 3-(4-methoxyphenyl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,3]triazolo[1,5-a]pyrazine (0.760 g, 33%): LC/MS (Table 2, Method a) Rt=2.74 min; MS m/z 420 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. temperaturethe mixture was heated to about 100° C. for about 15 min
  3. temperatureThe mixture was cooled to rt
  4. concentrationconcentrated on the under reduced pressure
  5. additionThe material was treated with water (100 mL) and EtOAc (˜40 mL)
  6. stirringThe mixture was stirred for about 10 min
  7. filtrationthen filtered
  8. washThe solids were washed with EtOAc (˜7 mL)
  9. customthen dried to a constant weight under vacuum at about 70° C.

Sources & evidence

ORD record
ord-74d06113bdec44388a67ed9af4e2671c
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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