tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-7-fluoro-3-oxo-4-(3-vinylisothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate → tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-(3-ethylisothiazol-5-yl)-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

HRID 2173061ノート

反応式

HRID 2173061 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[S:26][N:25]=[C:24]([CH:27]=[CH2:28])[CH:23]=3)[C:19]3[C:29](=[O:39])[N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][C:18]=3[C:17]=2[F:40])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[S:26][N:25]=[C:24]([CH2:27][CH3:28])[CH:23]=3)[C:19]3[C:29](=[O:39])[N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][C:18]=3[C:17]=2[F:40])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

参加物

4

反応物 1

HCID 86727256tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-7-fluoro-3-oxo-4-(3-vinylisothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

生成物 1

HCID 71164899tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-(3-ethylisothiazol-5-yl)-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate収率 94.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a stirred solution of tert-butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-7-fluoro-3-oxo-4-(3-vinylisothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (58 mg, 0.101 mmol) in MeOH (1.0 mL) was added Pd/C (30 mg, 0.282 mmol) under N2 atmosphere. The mixture was stirred at room temperature overnight under H2 atmosphere. The solids were removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (Flash 60 column) eluting with hexane/EtOAc (1:1) to give the title compound as a yellow solid (54.9 mg, 94%). 1H NMR (500 MHz, CDCl3) δ ppm 1.36 (t, J=7.57 Hz, 3H), 1.48 (br s, 9H), 1.61 (s, 9H), 1.71-1.82 (m, 1H), 2.20-2.33 (m, 1H), 2.91 (q, J=7.60 Hz, 2H), 3.64 (t, J=11.72 Hz, 1H), 3.74 (d, J=11.72 Hz, 1H), 3.91-3.99 (m, 1H), 4.01-4.10 (m, 2H), 4.23-4.34 (m, 1H), 4.72 (s, 2H), 5.37 (d, J=6.83 Hz, 1H), 6.47 (br s, 1H), 8.78 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C27H36FN5O6S, 578. found, 578.

後処理

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (Flash 60 column)
  4. washeluting with hexane/EtOAc (1:1)

出典と根拠

ORDレコード
ord-911a42d8700e47c18a99a5116ba7e093
出典データセット
uspto-grants-2015_06
特許番号
US09056873B2

反応ノート

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