HCID 89852127, compound → HCID 89852072, compound

HRID 1746898Notes

Reaction equation

HRID 1746898 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:12]=[CH:11][N:10]([C:13]3[N:23]=[CH:22][CH:21]=[CH:20][C:14]=3[C:15]([O:17]CC)=[O:16])[N:9]=2)[CH2:3][CH2:2]1>CO.O>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]2[CH:12]=[CH:11][N:10]([C:13]3[N:23]=[CH:22][CH:21]=[CH:20][C:14]=3[C:15]([OH:17])=[O:16])[N:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 89852127HCID 89852127, compound

Product 1

HCID 89852072HCID 89852072, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To ethyl 2-(3-(morpholinomethyl)-1H-pyrazol-1-yl)nicotinate (370 mg, 1.170 mmol) in methanol (20 mL) and water (2 mL) NaOH (2m solution; 1.7 mL) was added and the mixture heated to reflux for 90 min. The reaction mixture was concentrated, taken up in water, 1.7 mL of 2n HCl added and concentrated again. The obtained solid was treated with 20 mL of acetone, the remainder filtered off and dried to give 295 mg of the acid as off-white amorphous solid; ESI-MS [M+H]+: 289.2.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 90 min
  3. concentrationThe reaction mixture was concentrated
  4. addition1.7 mL of 2n HCl added
  5. concentrationconcentrated again
  6. additionThe obtained solid was treated with 20 mL of acetone
  7. filtrationthe remainder filtered off
  8. customdried

Sources & evidence

ORD record
ord-1d9196ee95774e148f197c2401b2377c
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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