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2-Azido-1-(4-methylphenyl)ethanone → N-[8-(5-p-methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]methanesulfonamide

HRID 600816
ノート
印刷プレビュー

反応式

HRID 600816 の反応式
[N:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][CH:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:10][CH2:9]2)=[C:2]=S.C(OC1CC2C(CC=1)=CC=CC=2N=C=S)C.[N:35]([CH2:38][C:39]([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)=[O:40])=[N+]=[N-].N(CC(C1C=CC(C(F)(F)F)=CC=1)=O)=[N+]=[N-]>>[CH3:47][C:44]1[CH:43]=[CH:42][C:41]([C:39]2[O:40][C:2]([NH:1][C:4]3[CH:5]=[CH:6][CH:7]=[C:8]4[C:13]=3[CH2:12][CH:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:10][CH2:9]4)=[N:35][CH:38]=2)=[CH:46][CH:45]=1
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 4

HCID 110084392-Azido-1-(4-methylphenyl)ethanoneHCID 534164932-Azido-1-[4-(trifluoromethyl)phenyl]ethanoneHCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthaleneHCID 86609616N-(8-Isothiocyanato-1,2,3,4-tetrahydronaphthalen-2-yl)methanesulfonamide

生成物 1

HCID 11964286N-[8-(5-p-methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]methanesulfonamide
収率 64.4%

実験手順

The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 23C (128 mg, 0.453 mmol) for the product of Example 1F and the product of Example 9A (95 mg, 0.544 mmol) for the product of Example 1G. The crude product was purified by flash chromatography eluting with 2% to 5% CH3OH/CH2Cl2 followed by 100% EtOAc which gave 116 mg (64%) of the title compound as a tan solid. 1H NMR (DMSO-d6) δ 9.13 (s, 1H), 7.61 (d, J=7.5 Hz, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.30 (s, 1H), 7.23 (m, 3H), 7.11 (t, J=7.8 Hz, 1H), 6.85 (d, J=7.5 Hz, 1H), 3.58 (m, 1H), 3.11 (m, 1H), 2.99 (s, 3H), 2.87 (m, 2H), 2.56 (m, 1H), 2.31 (s, 3H), 2.01 (m, 1H), 1.66 (m, 1H); MS (ESI+) m/z 398 (M+H)+.

後処理

  1. customThe title compound was prepared
  2. customThe crude product was purified by flash chromatography
  3. washeluting with 2% to 5% CH3OH/CH2Cl2

出典と根拠

ORDレコード
ord-f37863fa88cf4804b472eedd1d2cb0d2
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902236B2

反応ノート

読み込み中…

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