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2-Azido-1-(4-methylphenyl)ethanone → [8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester

HRID 600808
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HRID 600808 반응식
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([N:18]=[C:19]=S)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC1CC2C(CC=1)=CC=CC=2N=C=S)C.[N:38]([CH2:41][C:42]([C:44]1[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=1)=[O:43])=[N+]=[N-].N(CC(C1C=CC(C(F)(F)F)=CC=1)=O)=[N+]=[N-]>>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([NH:18][C:19]3[O:43][C:42]([C:44]4[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=4)=[CH:41][N:38]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 110084392-Azido-1-(4-methylphenyl)ethanoneHCID 534164932-Azido-1-[4-(trifluoromethyl)phenyl]ethanoneHCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthaleneHCID 86609614(8-Isothiocyanato-1,2,3,4-tetrahydronaphthalen-2-yl)carbamic acid tert-butyl ester

생성물 1

HCID 67229286[8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester
수율 83%

실험 절차

The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 20F (188 mg, 0.618 mmol) for the product of Example 1F and the product of Example 9A (130 mg, 0.741 mmol) for the product of Example 1G. The crude product was purified by flash chromatography eluting with 2% to 5% CH3OH/CH2Cl2 followed by 60% EtOAc/hexanes which gave 215 mg (83%) of the title compound as a yellow amorphous solid. 1H NMR (DMSO-d6) δ 9.06 (br s, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.45 (d, J=8.1 Hz, 2H), 7.29 (s, 1H), 7.23 (d, J=8.1 Hz, 2H), 7.10 (t, J=7.8 Hz, 1H), 6.98 (br d, 1H), 6.84 (d, J=7.5 Hz, 1H), 3.65 (m, 1H), 3.02 (m, 1H), 2.83 (m, 2H), 2.42 (m, 1H), 2.31 (s, 3H), 1.87 (m, 1H), 1.58 (m, 1H), 1.39 (s, 9H); MS (ESI+) m/z 420 (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-f5c45e1305cd48baa4f5f170cd6b7dc1
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902236B2

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