Hydrochloric Acid → HCID 67456106, compound

HRID 876698Notes

Reaction equation

HRID 876698 reaction equation
C([O:3][C:4](=O)[C:5]([N:21]1[CH:25]=[CH:24][N:23]=[N:22]1)=[CH:6][NH:7][NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:12]=[CH:11][N:10]=1)C.C[O-].[Na+].[ClH:30]>C(O)C.CO>[ClH:30].[N:15]1([C:13]2[N:12]=[CH:11][N:10]=[C:9]([N:8]3[C:4](=[O:3])[C:5]([N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)=[CH:6][NH:7]3)[CH:14]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 674548403-[2-(6-morpholin-4-ylpyrimidin-4-yl)hydrazino]-2-(1H-1,2,3-triazol-1-yl)prop-2-enoic acid ethyl ester

Product 1

HCID 67456106HCID 67456106, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

Batch 2: A further amount of the title compound is obtained as follows: The residue (2.4 g) obtained from the mother liquor during the synthesis of Example Compound 71, which contains the open-ring intermediate state of the cyclization, 3-[2-(6-morpholin-4-ylpyrimidin-4-yl)hydrazino]-2-(1H-1,2, 3-triazol-1-yl)prop-2-enoic acid ethyl ester, is dissolved in 12 ml ethanol and 1.5 ml 30% strength sodium methylate solution in methanol are added at RT, while stirring. The mixture is subsequently stirred at RT for 45 min, then adjusted to pH 5 with 2 N hydrochloric acid and subsequently stirred at RT for a further 16 h. The mixture is cooled to 10° C. and the solid is filtered off and washed with 3.5 ml dioxane. The mixture is dried under a high vacuum for 16 h, 5 ml methanol are then added and the mixture is subsequently stirred at RT for 1 h. The solid is filtered off, washed with 2 ml methanol and dried under a high vacuum to give a further 997 mg of the title compound in this way.

Workup

  1. stirringThe mixture is subsequently stirred at RT for 45 min
  2. stirringsubsequently stirred at RT for a further 16 h
  3. filtrationthe solid is filtered off
  4. washwashed with 3.5 ml dioxane
  5. customThe mixture is dried under a high vacuum for 16 h
  6. addition5 ml methanol are then added
  7. stirringthe mixture is subsequently stirred at RT for 1 h
  8. filtrationThe solid is filtered off
  9. washwashed with 2 ml methanol
  10. customdried under a high vacuum

Sources & evidence

ORD record
ord-a15b3791039a472ea37bdb91db50f188
Source dataset
uspto-grants-2015_03
Patent number
US08987261B2

Reaction notes

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