p-(Trifluoromethoxy)phenyl isocyanate → HCID 49780163, 화합물

HRID 929504노트

반응식

HRID 929504 반응식
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.[C:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C1COCC1>[F:1][C:2]([F:13])([F:14])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:12])[NH:28][CH:25]2[CH2:24][CH2:23][N:22]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:27][CH2:26]2)=[CH:8][CH:9]=1

참가 물질

4

반응물 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 12682914-Amino-1-Boc-piperidine

생성물 1

HCID 49780163HCID 49780163, 화합물수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-Trifluoromethoxyphenyl isocyanate (1.03 g, 5 mmol) was dissolved in dry THF (10 mL) and cooled in an ice bath. A solution of N—BOC-4-aminopiperidine (781 mg, 5 mmol) in dry THF (10 mL) was slowly added. The reaction was allowed to warm to RT and stir for 12 hours. The solvent was removed and the residue chromatographed from ethyl acetate to give intermediate 41 (1.71 g, 95%) as a white solid: Mp 160-162° C. 1H NMR (500 MHz, DMSO-d6) δ 8.54 (s, 1H), 7.47 (d, J=9.0 Hz, 2H), 7.21 (d, J=8.6 Hz, 2H), 6.22 (d, J=7.6 Hz, 1H), 3.81 (d, J=13.0 Hz, 2H), 3.67-3.59 (m, 1H), 2.90 (s, 2H), 1.79 (dd, J=12.6, 2.5 Hz, 2H), 1.40 (s, 9H), 1.25 (dq, J=12.1, 3.9 Hz, 2H). HRMS calculated for C18H24F3N3O4−H+402.1641. found (ESI(−), [M−H]) 402.1612.

후처리

  1. temperaturecooled in an ice bath
  2. customThe solvent was removed
  3. customthe residue chromatographed from ethyl acetate

출처 및 근거

ORD 기록
ord-62d4a2c0b0604116bcccef6b7b572e44
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296693B2

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