Hydrochloric Acid → N1-(5-p-methylphenyloxazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1,7-diamine

HRID 600809

반응식

HRID 600809 반응식
Cl.C(OC(=O)[NH:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([NH:19][C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)=[CH:23][N:24]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)(C)(C)C>O1CCOCC1>[CH3:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[O:21][C:20]([NH:19][C:12]3[C:11]4[CH2:10][CH:9]([NH2:8])[CH2:18][CH2:17][C:16]=4[CH:15]=[CH:14][CH:13]=3)=[N:24][CH:23]=2)=[CH:26][CH:27]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 67229286[8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester

생성물 1

HCID 11964240N1-(5-p-methylphenyloxazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1,7-diamine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

Hydrogen chloride in dioxane (4N, 7 mL, 28 mmol) was added to a suspension of 199 mg (0.474 mmol) of the product of Example 20G in 1 mL dioxane. After stirring 45 minutes, the mixture was quenched with 3N NaOH solution, then diluted with EtOAc and poured into water. The separated organic phase was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was triturated with Et2O and the solid was collected by vacuum filtration. The result was 92 mg (61%) of the title compound as a pale pink solid. 1H NMR (DMSO-d6) δ 9.02 (br s, 1H), 7.57 (d, J=7.1 Hz, 1H), 7.45 (d, J=8.1 Hz, 2H), 7.28 (s, 1H), 7.23 (d, J=8.1 Hz, 2H), 7.08 (t, J=7.8 Hz, 1H), 6.83 (d, J=7.1 Hz, 1H), 3.05-2.70 (m, 4H), 2.31 (m, 4H), 1.85 (m, 3H), 1.42 (m, 1H); MS (ESI+) m/z 320 (M+H)+.

후처리

  1. customthe mixture was quenched with 3N NaOH solution
  2. additiondiluted with EtOAc
  3. additionpoured into water
  4. washThe separated organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was triturated with Et2O
  9. filtrationthe solid was collected by vacuum filtration

출처 및 근거

ORD 기록
ord-c6b6c8bde45c42ea907b482b8340cf78
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902236B2

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