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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
ノート
印刷プレビュー

反応式

HRID 1484693 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-103990f77a67476e82dc52d8bc7a554e
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422268B2

反応ノート

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