Water → HCID 59651905, compound

HRID 221830Notes

Reaction equation

HRID 221830 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CC([O-])(C)C.[K+].O>CS(C)=O.CC(O)(C)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[N:12][NH:11][C:10](=[O:14])[CH:9]=3)=[CH:6][N:7]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 59652010HCID 59652010, compound

Product 1

HCID 59651905HCID 59651905, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 5-(6-chloropyridin-3-yl)-2H-pyridazin-3-one (73 mg, 0.35 mmol) and 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (140 mg, 0.70 mmol) in 2.7 mL of DMSO was stirred as KOtBu in 2-methyl-2-propanol (1.0 M, 14.4 mL) was added dropwise. After stirring at 110° C. overnight, the reaction was cooled to rt, and 2 mL of water was added. The mixture was extracted with CH2Cl2 (3×10 mL), the extracts combined and dried over Na2SO4. The crude product was purified by prep. TLC with 10% MeOH in CH2Cl2 to give 71 mg (54%) of 4-[5-(6-oxo-1,6-dihydropyridazin-4-yl)-pyridin-2-yloxy]piperidine-1-carboxylic acid tert-butyl ester; MS m/z 273 (M-Boc-H).

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction was cooled to rt
  3. extractionThe mixture was extracted with CH2Cl2 (3×10 mL)
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-cd1c7a1e0711481d9cf559d14afa7713
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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