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Sodium hydride → 2,4-dichloro-3-({5-cyclopropyl-3-[5-methoxy-4-(pyridin-4-ylamino) pyrimidin-2-yl]-4-methyl-1H-pyrazol-1-yl}methyl)benzoic acid

HRID 1484693
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1484693
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([C:9]3[N:14]=[C:13]([NH:15][C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[C:12]([O:22][CH3:23])=[CH:11][N:10]=3)[C:5]=2[CH3:24])[CH2:3][CH2:2]1.Br[CH2:26][C:27]1[C:28]([Cl:38])=[C:29]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:30]([O:32]C)=[O:31].[H-].[Na+]>C1COCC1>[Cl:38][C:28]1[C:27]([CH2:26][N:8]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[C:5]([CH3:24])[C:6]([C:9]3[N:14]=[C:13]([NH:15][C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[C:12]([O:22][CH3:23])=[CH:11][N:10]=3)=[N:7]2)=[C:36]([Cl:37])[CH:35]=[CH:34][C:29]=1[C:30]([OH:32])=[O:31]
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 15477480Methyl 3-(bromomethyl)-2,4-dichlorobenzoateHCID 896490232-(5-cyclopropyl-4-methyl-1H-pyrazol-3-yl)-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine

Produkt 1

HCID 716115972,4-dichloro-3-({5-cyclopropyl-3-[5-methoxy-4-(pyridin-4-ylamino) pyrimidin-2-yl]-4-methyl-1H-pyrazol-1-yl}methyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

200 mg of 2-(5-cyclopropyl-4-methyl-1H-pyrazol-3-yl)-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine 1-16-1 (0.62 mmol, 1.0 eq.), 184.86 mg of methyl 3-(bromomethyl)-2,4-dichlorobenzoate (0.62 mmol, 1.0 eq.) and 31.0 mg of 60% sodium hydride in paraffin oil were suspended in 6.3 mL of dry THF and stirred for 20 hours at rt. The reaction mixture was partitioned between water and DCM/propan-2-ol 4:1. The separated aqueous layer was extracted three times with DCM/propan-2-ol 4:1. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The purification by flash chromatography and preparative HPLC of the residue provided 37.5 mg (0.07 mmol, 11%) of analytically pure target compound.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and DCM/propan-2-ol 4:1
  2. extractionThe separated aqueous layer was extracted three times with DCM/propan-2-ol 4:1
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe purification by flash chromatography and preparative HPLC of the residue
  6. customprovided 37.5 mg (0.07 mmol, 11%) of analytically pure target compound

Quellen und Nachweise

ORD-Eintrag
ord-103990f77a67476e82dc52d8bc7a554e
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09422268B2

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