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Cesium carbonate → (R)-tert-butyl 3-((5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

HRID 1507494
ノート
印刷プレビュー

反応式

HRID 1507494 の反応式
I[C:2]1[C:3]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[N:4][C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:6][C:7]=1[O:8][CH3:9].[N:30]1([C:35]2[S:36][CH:37]=[C:38](B3OC(C)(C)C(C)(C)O3)[N:39]=2)[CH:34]=[CH:33][CH:32]=[CH:31]1.C([O-])([O-])=O.[Cs+].[Cs+]>[Pd+2].Cl[Cu].CN(C=O)C>[N:30]1([C:35]2[S:36][CH:37]=[C:38]([C:2]3[C:3]([NH:16][C@@H:17]4[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:18]4)=[N:4][C:5]([N:10]4[CH2:11][CH2:12][O:13][CH2:14][CH2:15]4)=[N:6][C:7]=3[O:8][CH3:9])[N:39]=2)[CH:34]=[CH:33][CH:32]=[CH:31]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 457859762-(1H-pyrrol-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazoleHCID 117677619Tert-butyl 3-((5-iodo-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

生成物 1

HCID 117677378(R)-tert-butyl 3-((5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 62652
Cuprous chloride
触媒
HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

In a 40 mL vial chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl)]-palladium(II) (0.023 g, 0.029 mmol), tert-butyl 3-((5-iodo-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate (Compound (21) (0.15 g, 0.289 mmol), 2-(1H-pyrrol-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (0.088 g, 0.318 mmol) and CuCl (0.031 g, 0.318 mmol) were combined. This mixture was then evacuated and backfilled with argon. Then DMF (2.89 ml) and Cs2CO3 (0.376 g, 1.16 mmol) were added to this flask all under argon. This mixture was then heated at 100° C. for 18 h. The mixture was cooled, filtered, diluted with ethyl acetate (mL), washed with water, then dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified via column chromatography. (0-50% EtOAc/hexane) to give the title compound as a white solid. MS (m/z)=542 (M+H).

後処理

  1. customThis mixture was then evacuated
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. additiondiluted with ethyl acetate (mL)
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified via column chromatography

出典と根拠

ORDレコード
ord-edfc0df8dce94c6fa712bd82958981d8
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09221809B2

反応ノート

読み込み中…

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