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

HRID 1785579

반응식

HRID 1785579 반응식
[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

참가 물질

5

반응물 4

HCID 110084392-azido-1-(4-methylphenyl)ethanoneHCID 53416493HCID 53416493, 화합물HCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthaleneHCID 86609616HCID 86609616, 화합물

생성물 1

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

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-4ca613d4c76f43b0a96578213c5ac505
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504520B2

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