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Tetrahydrofuran → HCID 118061539、化合物

HRID 920758
ノート
印刷プレビュー

反応式

HRID 920758 の反応式
[F:1][CH:2]([F:12])[O:3][CH2:4][C@@H:5]1[CH2:8][CH2:7][C@H:6]1C(O)=O.C1C=CC(P([N:27]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[Cl:30][C:31]1[CH:32]=[C:33]([C:38]2[C:46]([C:47]([NH2:49])=[O:48])=[C:41]3[CH2:42][NH:43][CH2:44][CH2:45][N:40]3[N:39]=2)[CH:34]=[CH:35][C:36]=1[F:37].C1[CH2:54][O:53]CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:30][C:31]1[CH:32]=[C:33]([C:38]2[C:46]([C:47]([NH2:49])=[O:48])=[C:41]3[CH2:42][N:43]([C:54]([NH:27][C@@H:6]4[CH2:7][CH2:8][C@H:5]4[CH2:4][O:3][CH:2]([F:1])[F:12])=[O:53])[CH2:44][CH2:45][N:40]3[N:39]=2)[CH:34]=[CH:35][C:36]=1[F:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 199401P,P-Diphenylphosphinic azideHCID 1180616272-(3-Chloro-4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-3-carboxamideHCID 118061920HCID 118061920、化合物

生成物 1

HCID 118061539HCID 118061539、化合物収率 20%

試薬・触媒・溶媒 2

HCID 1140
Toluene
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A stirred solution of Intermediate 241B (18.34 mg, 0.102 mmol) in toluene (1 mL) at RT under nitrogen was added TEA (0.043 mL, 0.305 mmol), DPPA (0.047 mL, 0.204 mmol) and the reaction mixture was heated at 70° C. for 2 h. The reaction mass was cooled to RT and to it was added a solution of Intermediate 185B (30 mg, 0.102 mmol) in THF (1 mL) and stirred for 16 h. The reaction mass was diluted with ethyl acetate (5 mL) and the organic layer was separated. The organic layer was washed sequentially with an aqueous solution of 10% NaHCO3, water, and brine, then dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford Compound 241 as pale yellow solid (10 mg, 20% yield). The HPLC Retention times are 1.453 min. and 1.467 min. (Methods J and K respectively); MS(ES): m/z=472.2[M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.85 (dd, J=7.28, 2.13 Hz, 1H), 7.69 (ddd, J=8.63, 4.80, 2.13 Hz, 1H), 7.39-7.52 (m, 1H), 7.11-7.33 (2bs, 2H), 7.10 (d, J=7.34 Hz, 1H), 6.36-6.88 (m, 1H), 4.73 (s, 2H), 4.13 (t, J=5.27 Hz, 2H), 3.72-3.99 (m, 5H), 2.00-2.16 (m, 1H), 1.68-1.94 (m, 2H), 1.33-1.53 (m, 1H).

後処理

  1. temperatureThe reaction mass was cooled to RT and to it
  2. customthe organic layer was separated
  3. washThe organic layer was washed sequentially with an aqueous solution of 10% NaHCO3, water, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-e925641210974c84a1e3e5788fd73bf5
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273058B2

反応ノート

読み込み中…

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