Water → HCID 11964255, 화합물

HRID 600775

반응식

HRID 600775 반응식
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[CH2:23][C:22](=[O:25])[CH2:21][CH2:20]4)=[N:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].O>C(O)C>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]4)=[N:11][CH:10]=2)=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 119558408-{5-[4-(Trifluoromethyl)phenyl]oxazol-2-ylamino}-3,4-dihydronaphthalen-2(1H)-one

생성물 1

HCID 11964255HCID 11964255, 화합물수율 56.4%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

The product of Example 1I (60 mg, 0.161 mmol) in ethanol (6 mL) was treated at 0° C. with NaBH4 (7 mg, 0.184 mmol). The reaction was stirred at 0° C. for 1 hour and was then poured into H2O and extracted with ethyl acetate. The extracts were dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 70%-85% ethyl acetate-hexane to afford the title compound as a tan solid (34 mg, 56%). 1H NMR (DMSO-d6) δ 9.33 (s, 1H), 7.78 (m, 4H), 7.62 (s, 1H), 7.55 (d, 1H, J=7.4 Hz), 7.11 (m, 1H), 6.88 (d, 1H, J=7.2 Hz), 4.83 (d, 1H, J=4.1 Hz), 3.92 (m, 1H), 2.69-2.98 (m, 4H), 1.86 (m, 1H), 1.62 (m, 1H); MS (ESI+) m/z 375 (M+H).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 70%-85% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-8bf866afe58340a190e1428e2f932e2c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902236B2

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