Water → HCID 21105611, compound

HRID 2426683Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:30]=[CH:29][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][CH2:24][CH:23]([N:26]([CH3:28])[CH3:27])[CH2:22]3)=[CH:17][CH:16]=2)=[O:13])=[CH:10][N:9]=1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH3:27][N:26]([CH3:28])[CH:23]1[CH2:24][CH2:25][N:21]([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[C:11]3[CH:29]=[CH:30][C:8]([O:38][C:35]4[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=4)=[N:9][CH:10]=3)=[CH:16][CH:17]=2)[CH2:22]1

Participants

Conditions

Temperature: 140 °C

Procedure

49 mg of potassium carbonate were added to a solution of 0.041 g of 6-chloro-N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]nicotinamide and 4-fluorophenol (30 mg) in 0.8 ml of DMF, and the reaction was heated at 140° C. in a microwave apparatus for 90 minutes. After addition of water and ethyl acetate, the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, concentrated in vacuo and purified by preparative HPLC. This resulted in the product with the molecular weight of 420.2 (C24H25FN4O2); MS (ESI): 421 (M+H+) as hydrotrifluoroacetate.

Workup

extractionthe aqueous phase was extracted three times with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by preparative HPLC
customThis resulted in the product with the molecular weight of 420.2 (C24H25FN4O2)

Sources & evidence

ORD record: ord-44229ee36d4f4a398d4bfb8a7367db5d
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968550B2

Reaction notes

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