Diisopropylethylamine → HCID 86726719、化合物

HRID 1499489ノート

反応式

HRID 1499489 の反応式
I[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[O:11][CH2:12][CH2:13][C:3]=12.[CH3:14][C@H:15]1[CH2:20][NH:19][CH2:18][C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16]1.CCN(C(C)C)C(C)C>CCO>[CH3:14][C@H:15]1[CH2:20][N:19]([C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]3[O:11][CH2:12][CH2:13][C:3]=23)[CH2:18][C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 57433105tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamateHCID 867266754-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine

生成物 1

HCID 86726719HCID 86726719、化合物収率 75%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To a microwave vial containing 4-iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine (from Example 9, step 3) (47.8 mg, 0.164 mmol) and tert-butyl [(3S,5R)-5-methylpiperidin-3-yl]carbamate (33.7 mg, 0.157 mmol), EtOH (1.00 mL) was added, followed by DIPEA (41.5 mg, 0.321 mmol). The mixture was heated under microwave irradiation at 100° C. for 2 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the title compound as a yellow solid (44.5 mg, 75%). LCMS calc. for C18H27N4O5 (M+H)+: m/z=379.2. found 379.2.

後処理

  1. additionwas added
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-abc8d633c63e49b6a8e4d2e94cb5f488
出典データセット
uspto-grants-2015_12
特許番号
US09200004B2

反応ノート

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