Water → N-[4-(6-{[(1S)-1-Phenylethyl]amino}pyrazin-2-yl)phenyl]methanesulfonamide

HRID 1244409ノート

反応式

HRID 1244409 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH:11]=[N:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>C1COCC1>[C:17]1([C@@H:15]([NH:14][C:12]2[N:13]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:7][CH:6]=3)[CH:9]=[N:10][CH:11]=2)[CH3:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 587170936-(4-aminophenyl)-N-[(1S)-1-phenylethyl]pyrazin-2-amine

生成物 1

HCID 58717098N-[4-(6-{[(1S)-1-Phenylethyl]amino}pyrazin-2-yl)phenyl]methanesulfonamide収率 73.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 6-(4-aminophenyl)-N-[(1S)-1-phenylethyl]pyrazin-2-amine (58 mg, 0.2 mmol) in dry THF (3 mL) was added triethylamine (70 μL, 0.5 mmol). The solutions was cooled to 0° C. and methanesulphonyl chloride (18.6 μL, 0.24 mmol) was added dropwise. The mixture was allowed to warm to RT and stirred overnight, before dilution with water (15 mL). The product was extracted into ethyl acetate (2×15 mL) and the combined extracts washed with 10% aqueous Na2CO3 and brine, and then dried (Na2SO4). The solvent was removed under reduced pressure and the product purified by chromatography eluting with ethyl acetate-hexane (3:2) to afford the product as a pale yellow solid (54 mg, 73%).

後処理

  1. temperatureto warm to RT
  2. extractionThe product was extracted into ethyl acetate (2×15 mL)
  3. washthe combined extracts washed with 10% aqueous Na2CO3 and brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe product purified by chromatography
  7. washeluting with ethyl acetate-hexane (3:2)

出典と根拠

ORDレコード
ord-bca8734e607549a29d525598cf33a01d
出典データセット
uspto-grants-2006_10
特許番号
US07122550B2

反応ノート

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