Methanol → HCID 86702119, compound

HRID 873605Notes

Reaction equation

HRID 873605 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:19][N:18]([C:20]4[N:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:17]3)=[O:15])=[CH:9][CH:8]=2)=[CH:5][C:4]([C:26]([O:28]CC)=[O:27])=[N:3]1.CO.[OH-].[Li+]>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:19][N:18]([C:20]4[N:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:17]3)=[O:15])=[CH:9][CH:8]=2)=[CH:5][C:4]([C:26]([OH:28])=[O:27])=[N:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86702120HCID 86702120, compound

Product 1

HCID 86702119HCID 86702119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1-methyl-5-(4-(1-(pyridazin-3-yl)azetidine-3-carboxamido)phenyl)-1H-pyrazole-3-carboxylate (368 mg, 0.905 mmol) was taken up in tetrahydrofuran (3.38 mL), and methanol (3.38 mL) then 1N aqueous lithium hydroxide (1.35 mL, 1.350 mmol) was added. The mixture was heated at 60° C. for 2 hours. The mixture was concentrated to dryness, suspended in water and treated with 1N aqueous HCl to pH 2. The solution was extracted with ethyl acetate and the organic layers were dried with sodium sulfate, filtered, and concentrated to give a colorless syrup that solidified upon standing. This solid was triturated with ether and collected by filtration to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.67 (s, 1H), 10.32 (bs, 1H), 8.60-8.55 (m, 1H), 7.77 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.42 (dd, J=9.0, 4.5 Hz, 1H), 6.89 (d, J=8.9 Hz, 1H), 6.80 (s, 1H), 4.34-4.13 (m, 4 H), 3.91 (s, 3 H), 3.83-3.74 (m, 1H); MS (ESI(+)) m/e 379 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with 1N aqueous HCl to pH 2
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialthe organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless syrup that
  8. customThis solid was triturated with ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5988cd58e55a4631b1cf6e0a59767ee0
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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