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Tetrahydrofuran → N-(2-((3-(dimethylamino)propyl)(methyl)amino)-5-(trifluoromethyl)phenyl)-2-fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzamide

HRID 883032
Notes
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Reaction equation

HRID 883032 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]([C:18]3[O:22][CH:21]=[N:20][CH:19]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:23][N:24]([CH3:41])[CH2:25][CH2:26][CH2:27][N:28]([CH3:40])[C:29]1[C:30]([NH2:39])=[CH:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=1.C1COCC1>C(N(CC)CC)C>[CH3:41][N:24]([CH3:23])[CH2:25][CH2:26][CH2:27][N:28]([CH3:40])[C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:31][C:30]=1[NH:39][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([O:11][C:12]2[C:17]([C:18]3[O:22][CH:21]=[N:20][CH:19]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:10][C:2]=1[F:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 16109009N~1~-[3-(dimethylamino)propyl]-N~1~-methyl-4-(trifluoromethyl)benzene-1,2-diamineHCID 866237882-Fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzoyl chloride

Product 1

HCID 25102087N-(2-((3-(dimethylamino)propyl)(methyl)amino)-5-(trifluoromethyl)phenyl)-2-fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzamide

Reagents, catalysts & solvents 1

HCID 8471
Triethylamine
Solvent

Procedure

To 2-fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzoyl chloride (60 mg, 0.17 mmol) and N1-(3-(dimethylamino)propyl)-N1-methyl-4-(trifluoromethyl)benzene-1,2-diamine (44.1 mg, 0.160 mmol) was added THF (1.0 mL). The mixture was stirred at rt for 4.5 days. The reaction was quenced with excess triethylamine, filtered and concentrated. The residue was purified by Gilson reverse-phase HPLC (0.1% TFA in water/acetonitrile). After basic workup, N-(2-((3-(dimethylamino)propyl)(methyl)amino)-5-(trifluoromethyl)phenyl)-2-fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzamide was obtained as a white solid. MS m/z=558 [M+1]+. Calc'd for C28H27F4N5O3: 557.55.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by Gilson reverse-phase HPLC (0.1% TFA in water/acetonitrile)

Sources & evidence

ORD record
ord-6b6e2238281241e8ba72c5b08639b66d
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236823B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes