p-(Trifluoromethoxy)phenyl isocyanate → HCID 49780163、化合物

HRID 929504ノート

反応式

HRID 929504 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 49780163HCID 49780163、化合物収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-62d4a2c0b0604116bcccef6b7b572e44
出典データセット
uspto-grants-2016_03
特許番号
US09296693B2

反応ノート

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