Potassium Iodide → HCID 68638032, compound

HRID 639992Notes

Reaction equation

Cl.Cl[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:17][C:18]3[CH:19]=[N:20][N:21]([CH2:23][C:24]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=4[F:34])=[O:25])[CH:22]=3)=[N:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1.[C:35]1(=[O:45])[NH:39][C:38](=[O:40])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]12.[K].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(=O)([O-])O.[Na+]>CC(N(C)C)=O.C(OCC)C>[F:34][C:28]1[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:27]=1[NH:26][C:24](=[O:25])[CH2:23][N:21]1[CH:22]=[C:18]([NH:17][C:11]2[C:10]3[C:15](=[CH:16][C:7]([O:6][CH2:5][CH2:4][CH2:3][N:39]4[C:35](=[O:45])[C:36]5[C:37](=[CH:41][CH:42]=[CH:43][CH:44]=5)[C:38]4=[O:40])=[CH:8][CH:9]=3)[N:14]=[CH:13][N:12]=2)[CH:19]=[N:20]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-(4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide hydrochloride (0.25 g, 0.49 mmol), potassium phthalimide (0.109 g, 0.59 mmol), potassium carbonate (0.081 g, 0.59 mmol) and potassium iodide (0.098 g, 0.59 mmol) in dimethylacetamide (2 ml) was heated at 75° C. for 16 hours. The reaction mixture was allowed to cool to room temperature. Aqueous sodium hydrogen carbonate was added to the mixture and the resultant precipitate was filtered and washed with water, acetonitrile then diethyl ether to give N-(2,3-difluorophenyl)-2-[4-({7-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]quinazolin-4-yl}amino)-1H-pyrazol-1-yl]acetamide (0.214 g, 75% yield):

Workup

temperatureto cool to room temperature
filtrationthe resultant precipitate was filtered
washwashed with water, acetonitrile

Sources & evidence

ORD record: ord-6573f615084440eda50337a9b3d860ed
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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