Acetonitrile → HCID 58613334, compound

HRID 2054137Notes

Reaction equation

HRID 2054137 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[CH:5]=[CH:4][N:3]=1.[C:10]([NH:12][C:13](=[N:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:24][CH:23]=1)OC1C=CC=CC=1)#[N:11].C(=O)(O)[O-].[Na+].C(#N)C>CN1C(=O)CCC1.CCN(C(C)C)C(C)C>[NH2:11][C:10]1[N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[N:9]=[C:13]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:24][CH:23]=2)[N:12]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 211064422-Chloro-4-hydrazinylpyridineHCID 85974504HCID 85974504, compound

Product 1

HCID 58613334HCID 58613334, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
220 °C

Procedure

A microwave reaction vessel was charged with 1.34 g of (2-Chloro-pyridin-4-yl)-hydrazine (7.48 mmol, 1.1 equiv) and 2.00 g of N-cyano-N′-(4-acetamidophenyl)-O-phenylisourea (6.80 mMol, 1 equiv). The solids were dissolved in 40 mL of NMP and 8 mL of DIEA. The sealed vessel was warmed to 220° C. for 6 min via microwave irradiation. Upon cooling, the resulting solution was poured into 200 mL of saturated sodium bicarbonate. The precipitate was collected and washed with 3×100 mL of water. After azeotropic drying (3×50 mL of acetonitrile) the dark yellow solid (2.0 g, 5.80 mMol, 85% yield) was used without further purification. 1H NMR (500 Mhz, DMSO-d6) δ 9.68 (1 H, s), 9.00 (1 H, s), 8.40 (1 H, d), 7.67 (2 H, m), 7.50 (2 H, d), 7.40 (2 H, d), 6.95 (2 H, s), 2.0 (3 H, s) ppm. LCMS: 2.16 minutes/343.95 (M+H).

Workup

  1. customA microwave reaction vessel
  2. temperatureUpon cooling
  3. customThe precipitate was collected
  4. washwashed with 3×100 mL of water

Sources & evidence

ORD record
ord-1328f057dd864d848753c241aa446db8
Source dataset
uspto-grants-2008_02
Patent number
US07329652B2

Reaction notes

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