Potassium Iodide → N-Isopropyl-N-(4-methoxy-phenyl)-2-[2-(1,3,5-trimethyl-1H-pyrazol-ylamino)-phenylamino]-acetamide

HRID 1599083Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:9]2[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]([CH3:16])=[N:3]1.Br[CH2:18][C:19]([N:21]([CH:30]([CH3:32])[CH3:31])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.C(Cl)Cl>[CH:30]([N:21]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:19](=[O:20])[CH2:18][NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:5]1[C:4]([CH3:16])=[N:3][N:2]([CH3:1])[C:6]=1[CH3:7])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-benzene-1,2-diamine (7.56 g, 35.0 mmol) and 2-bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (7.18 g, 38.5 mmol) in DMF (70 mL) was added potassium carbonate (14.5 g, 105 mmol) and potassium iodide (581 mg, 3.5 mmol). The solution was heated at 80° C. for 15 h and subsequently poured into DCM (100 mL). The mixture was extracted with H2O (×4), 1N HCl (×2) and brine, dried over MgSO4 and concentrated in vacuo. The resulting foam was purified by trituration with Et2O to yield the title compound (11.9 g):

Workup

extractionThe mixture was extracted with H2O (×4), 1N HCl (×2) and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe resulting foam was purified by trituration with Et2O

Sources & evidence

ORD record: ord-dc2691803b224eccb7bfe2dc39d9ffec
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739129

Reaction notes

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