Pyridine → HCID 42626045, compound

HRID 1864639Notes

Reaction equation

HRID 1864639 reaction equation
[C:1](Cl)(Cl)=[O:2].N1C=CC=CC=1.[NH2:11][C:12]1[C:17]([NH2:18])=[C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:22][CH:21]=2)[CH:15]=[CH:14][N:13]=1.C1(C)C=CC=CC=1>C1COCC1>[O:2]=[C:1]1[NH:11][C:12]2=[N:13][CH:14]=[CH:15][C:16]([O:19][C:20]3[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[CH:24][CH:25]=3)=[C:17]2[NH:18]1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 1140TolueneHCID 6371Phosgene2×HCID 42625416Tert-butyl 4-(2,3-diaminopyridin-4-yloxy)phenylcarbamate

Product 1

HCID 42626045HCID 42626045, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Method E2 (with phosgene and pyridine). tert-Butyl 4-(2,3-diaminopyridin-4-yl-oxy)phenyl-carbamate (1 g, 3.16 mmol) was dissolved in dry THF (32 mL, 10 mL/mmol). The solution was cooled in an ice bath under nitrogen. Pyridine (0.59 mL, 7.27 mmol) was added and followed by dropwise addition a phosgene solution 1.93 M in toluene (2 mL, 3.79 mmol) under vigourous stirring. The ice bath was removed and the mixture was stirred at room temperature overnight, then at 60° C. during 2 hours. The solvent was evaporated under reduced pressure and the solid residue was washed with water and dried to afford the title compound (952 mg, 88%) as a brown solid. 1H-NMR (δ, ppm, DMSO-d6): 1.48 (9H, s, t-Bu), 6.29 (d, 1H, HPy,5, J=6.0 Hz), 7.09 (d, 2H, Harom,Ph,3+5, J=9.0 Hz), 7.51 (d, 2H, Harom,Ph,2+6, J=9.0 Hz), 7.73 (d, 1H, HPy,6, J=6.0 Hz), 9.43 (bs, 1H, NHBoc), 11.16 (bs, 1H, NHPy3) 11.34 (bs, 1H, NHPy2).; LC-MS (m/z): 343 (M+H, 100).

Workup

  1. temperatureThe solution was cooled in an ice bath under nitrogen
  2. customThe ice bath was removed
  3. waitat 60° C. during 2 hours
  4. customThe solvent was evaporated under reduced pressure
  5. washthe solid residue was washed with water
  6. customdried

Sources & evidence

ORD record
ord-2b2ed0d87a2f407db9b776581fe0b0c6
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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