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Trifluoroacetic acid → 2-(2-(2-(5-Chloro-2-(1-(piperidin-4-yl)-1H-pyrazol-4-ylamino)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592425
ノート
印刷プレビュー

反応式

HRID 592425 の反応式
[NH2:1][C:2](=[O:39])[CH:3]([C:5]1[CH:38]=[CH:37][CH:36]=[CH:35][C:6]=1[CH2:7][CH2:8][C:9]1[C:14]([Cl:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]2[CH:18]=[N:19][N:20]([CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[CH:21]=2)[N:10]=1)[CH3:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:15][C:14]1[C:9]([CH2:8][CH2:7][C:6]2[CH:35]=[CH:36][CH:37]=[CH:38][C:5]=2[CH:3]([CH3:4])[C:2]([NH2:1])=[O:39])=[N:10][C:11]([NH:16][C:17]2[CH:18]=[N:19][N:20]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:21]=2)=[N:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86712309tert-Butyl 4-(4-(4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)piperidine-1-carboxylate

生成物 1

HCID 732947842-(2-(2-(5-Chloro-2-(1-(piperidin-4-yl)-1H-pyrazol-4-ylamino)pyrimidin-4-yl)ethyl)phenyl)propanamide収率 26%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of tert-butyl 4-(4-(4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)piperidine-1-carboxylate A32 (0.090 g, 0.162 mmol) in DCM (5 mL) was added TFA (2.0 mL) and the mixture was stirred at room temperature for 1.5 hours. The solvent was removed and the residue was suspended in EtOAc (5 mL) and washed with 1M HCl. The aqueous layer was basified with 1M NaOH and extracted with EtOAc (2×5 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give a crude purple oil which was purified by flash chromatography (Combiflash Rf, 0-30% MeOH in DCM) to give the title compound 43 as a red oil (0.019 g, 26% yield). LCMS-C: rt 4.24 min; m/z 454 [M+H]+.

後処理

  1. customThe solvent was removed
  2. washwashed with 1M HCl
  3. extractionextracted with EtOAc (2×5 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude purple oil which
  8. customwas purified by flash chromatography (Combiflash Rf, 0-30% MeOH in DCM)

出典と根拠

ORDレコード
ord-40abdb4367ac43649476e2692da66e12
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238644B2

反応ノート

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