HCID 1252891, compound → HCID 85471831, compound

HRID 589808Notes

Reaction equation

HRID 589808 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)=[O:13])=[CH:7][C:3]=1[C:4](O)=O.[NH2:19][C:20]1[C:25]([NH2:26])=[CH:24][C:23]([CH3:27])=[CH:22][N:21]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)=[O:13])=[CH:7][C:3]=1[C:4]1[NH:26][C:25]2[C:20]([N:19]=1)=[N:21][CH:22]=[C:23]([CH3:27])[CH:24]=2

Participants

3

Reactant 2

HCID 1252891HCID 1252891, compoundHCID 107018255-Methylpyridine-2,3-diamine

Product 1

HCID 85471831HCID 85471831, compoundYield 6%

Conditions

Temperature
150 °C

Procedure

In a 40 mL vial was transferred 2-chloro-5-(furan-2-carboxamido)benzoic acid (I-1) (1 g, 3.75 mmol) in polyphosphoric acid (10 mL), and the 2,3-diamino-5-methyl-pyridine (578 mg, 4.69 mmols, 1.25 eq) was added. The dark brown reaction mixture was heated at 150° C. for 4 hrs. The reaction mixture was then quenched with solid sodium carbonate and extracted with ethyl acetate (3×50 mL). The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-100 EtOAC/Hex), afforded 80 mg (0.22 mmols, 6%) of the title compound (Example 1). 1H NMR (400 MHz, MeOD) δ 8.36-8.25 (m, 1H), 8.20 (s, 1H), 8.04-7.94 (m, 1H), 7.93-7.83 (m, 1H), 7.77 (s, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.31 (d, J=3.5 Hz, 1H), 6.67 (dd, J=1.7, 3.5 Hz, 1H), 2.53 (s, 3H). LCMS M/Z=353.0 (M+1). RT=1.39: Method B.

Workup

  1. customThe reaction mixture was then quenched with solid sodium carbonate
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (0-100 EtOAC/Hex)

Sources & evidence

ORD record
ord-df2c050c3c954eb1a7473492eed342c7
Source dataset
uspto-grants-2016_01
Patent number
US09233961B2

Reaction notes

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