Picolinic acid → HCID 56592241, compound

HRID 1616083Notes

Reaction equation

HRID 1616083 reaction equation
C(N(CC)CC)C.Cl.[F:9][C:10]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=1[NH:20][C:21]1[C:22]2[O:29][CH:28]=[C:27]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:23]=2[N:24]=[CH:25][N:26]=1.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42](O)=[O:43].Cl.C(N=C=NCCCN(C)C)C>O.C(Cl)Cl>[F:9][C:10]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:17])=[O:18])[CH:13]=[CH:12][C:11]=1[NH:20][C:21]1[C:22]2[O:29][CH:28]=[C:27]([CH:30]3[CH2:35][CH2:34][N:33]([C:42]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=4)=[O:43])[CH2:32][CH2:31]3)[C:23]=2[N:24]=[CH:25][N:26]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86681873HCID 86681873, compound

Product 1

HCID 56592241HCID 56592241, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, anhydrous methylene chloride (0.5 mL) and triethylamine (10 μL, 0.069 mmol) were added to N-[2-fluoro-4-(methylsulfonyl)phenyl]-7-(piperidin-4-yl)furo[3,2-d]pyrimidine-4-amine hydrochloride (10 mg, 0.023 mmol), picolinic acid (3.3 mg, 0.028 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9 mg, 0.046 mmol) and N,N-dimethylaminopyridine (0.3 mg, 0.002 mmol), followed by stirring at room temperature for 2 hours. Water was added to the reaction liquid, the reaction liquid was extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=20:1) to give the titled compound (3.3 mg, 35%) as a yellow oily substance.

Workup

  1. customthe reaction liquid
  2. extractionwas extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customthe obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-7067569094344fc1ad1693b2ef8b4030
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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