Potassium Iodide → HCID 56848547, compound

HRID 1801901Notes

Reaction equation

HRID 1801901 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[I-].[K+].CCN(C(C)C)C(C)C.Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=2)[N:23]=[C:22]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[O:32])[N:21]=1>CN(C=O)C>[F:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([NH:7][C:4]3[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=3)=[N:21][C:22]([C:31]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[O:32])=[N:23]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 86649052HCID 86649052, compound

Product 1

HCID 56848547HCID 56848547, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methyl-1H-pyrazol-3-amine (13 mg, 0.13 mmol), potassium iodide (15 mg, 0.088 mmol), and DIEA (0.016 mL, 0.088 mmol) in DMF (2 mL) was added to (4-chloro-7-fluoroquinazolin-2-yl)(4-fluorophenyl)methanone (0.027 mg, 0.088 mmol). The resulting solution was stirred at rt overnight and then purified by preparative HPLC (Varian diphenyl reverse phase column, eluted with gradient of solvent B=0.05% HOAC/CH3CN and solvent A=0.05% HOAc/H2O) to give (7-fluoro-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanone (10 mg, 31%). 1H NMR (300 MHz, DMSO-d6) δ 2.18 (s, 3H), 6.48 (s, 1H), 7.36 (t, 2H), 7.60 (m, 2H), 8.09 (m, 2H), 8.29 (t, 1H), 10.78 (s, 1H), 12.23 (s, 1H); LC-MS (ESI) m/z 366 (M+H)+.

Workup

  1. custompurified by preparative HPLC (Varian diphenyl reverse phase column
  2. washeluted with gradient of solvent B=0.05% HOAC/CH3CN and solvent A=0.05% HOAc/H2O)

Sources & evidence

ORD record
ord-d1a840a5319d4f25b852ba9ef5b2a83e
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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