Cyclopropanecarboxaldehyde → HCID 178515742, compound

HRID 1890322Notes

Reaction equation

HRID 1890322 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]([F:19])([F:18])[F:17].[CH:21]1([CH:24]=O)[CH2:23][CH2:22]1>[N+](C1C=CC=CC=1)([O-])=O>[CH:21]1([C:24]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:17])[F:18])[C:7]3=[N:6][C:5]([OH:20])=[CH:4][CH:3]=[C:2]3[N:1]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 178507772HCID 178507772, compound

Product 1

HCID 178515742HCID 178515742, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

5-Amino-6-(2-(trifluoromethoxy)phenylamino)pyridin-2-ol (0.10 g, 0.32 mmol) was dissolved in nitrobenzene (0.5 mL). Cyclopropanecarbaldehyde (0.044 g, 0.64 mmol) was added. The reaction mixture was heated to 120° C. overnight. After cooling, hexanes was added to the reaction mixture to form a precipitate. The precipitate was collected, washed with hexanes, and purified via HPLC to give the title compound (11 mg). LCMS m/z=336.2 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 1.35 (m, 4H), 2.03 (m, 1H), 6.86 (d, J=8.8 Hz, 1H), 7.71 (m, 2H), 7.83 (m, 2H), 7.83 (d, J=8.8 Hz, 1H).

Workup

  1. temperatureAfter cooling
  2. customto form a precipitate
  3. customThe precipitate was collected
  4. washwashed with hexanes
  5. custompurified via HPLC

Sources & evidence

ORD record
ord-72807ce3f41d4c05a0a41b52d5afd903
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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