HCID 66855372, compound → HCID 46866674, compound

HRID 2402451Notes

Reaction equation

HRID 2402451 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[C:6]([C:16]2[NH:17][CH2:18][CH2:19][N:20]=2)[S:5][C:4]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([CH:30]2[CH2:32][CH2:31]2)=[O:29])[CH:22]=1)#[N:2]>C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[C:6]([C:16]2[NH:20][CH:19]=[CH:18][N:17]=2)[S:5][C:4]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([CH:30]2[CH2:32][CH2:31]2)=[O:29])[CH:22]=1)#[N:2]

Participants

4

Reactant 1

HCID 66855372HCID 66855372, compound

Product 1

HCID 46866674HCID 46866674, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-{4-[3-cyano-4-(2,4-dichlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)-2-thienyl]pyridin-2-yl}cyclopropanecarboxamide (0.0650 g, 0.135 mmol) and Magtrieve (0.143 g, 1.70 mmol) was taken up in toluene (5 mL) and heated at 120° C. for 4 hours. The mixture was cooled to room temperature, diluted with DCM (10 mL) and filtered through a pad of celite. The solid residue was washed with 1% ammonia, 9% methanol in DCM mixture (10 mL) and solvent from the filtrate was evaporated. The residue was purified using ISCO chromatography on silica gel, elution 10 to 70% ethyl acetate in hexanes to afford the product (0.027 g, 47%). LCMS: (FA) ES+, 480, 482. 1H NMR (400 MHz, d6-DMSO) δ: 11.88 (s, 1H) 11.11 (m, 1H), 8.57-8.55 (m, 1H), 8.53-8.50 (m, 1H), 7.85-7.84 (m, 1H), 7.58-7.56 (m, 2H), 7.54-7.52 (m, 1H), 7.17-7.16 (m, 1H), 7.00-6.98 (m, 1H), 2.08-2.00 (m, 1H), 0.87-0.81 (m, 4H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washThe solid residue was washed with 1% ammonia, 9% methanol in DCM mixture (10 mL) and solvent from the filtrate
  4. customwas evaporated
  5. customThe residue was purified
  6. washon silica gel, elution 10 to 70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4fb3e1cd09ae43b3869ff59740acf210
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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