Water → HCID 46892627, compound

HRID 1801910Notes

Reaction equation

HRID 1801910 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[I-].[K+].[F:10][C:11]1[CH:48]=[CH:47][C:14]([C:15]([C:17]2[N:26]=[C:25](C3C(C(C)C)=C(S([O-])(=O)=O)C(C(C)C)=CC=3C(C)C)[C:24]3[C:19](=[CH:20][C:21]([CH3:46])=[CH:22][CH:23]=3)[N:18]=2)=[O:16])=[CH:13][CH:12]=1.O>CC(N(C)C)=O>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([C:17]2[N:26]=[C:25]([NH:7][C:4]3[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=3)[C:24]3[C:19](=[CH:20][C:21]([CH3:46])=[CH:22][CH:23]=3)[N:18]=2)=[O:16])=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 86649054HCID 86649054, compound

Product 1

HCID 46892627HCID 46892627, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 5-methyl-1H-pyrazol-3-amine (225 mg, 2.31 mmol), potassium iodide (188 mg, 0.088 mmol), and 2-(4-fluorobenzoyl)-7-methylquinazolin-4-yl2,4,6-triisopropylbenzenesulfonate (380 mg, 0.69 mmol) in DMA (2 mL) was stirred at 50° C. for 6 h, then water was added and the solution was filtered. The solid was then dried and triturated with acetonitrile to give (4-fluorophenyl)(7-methyl-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone (36 mg, 14%). 1H NMR (300 MHz, DMSO-d6) δ 2.18 (s, 3H), 2.50 (s, 3H), 6.53 (s, 1H), 7.38 (t, 2H), 7.51 (d, 2H), 7.66 (s,1H), 8.08 (m, 2H), 8.62 (d, 1H), 10.57 (s, 1H), 12.18 (s, 1H); LC-MS (ESI) m/z 362 (M+H)+.

Workup

  1. filtrationthe solution was filtered
  2. customThe solid was then dried
  3. customtriturated with acetonitrile

Sources & evidence

ORD record
ord-756ded0a306f4a6bb4e23bb150e931fc
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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