Selectfluor → (R)-tert-Butyl 1-(7-fluoro-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-3-methoxypropan-2-ylcarbamate

HRID 2092847ノート

反応式

HRID 2092847 の反応式
[CH3:1][O:2][CH2:3][C@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:5][NH:6][C:7]1[N:12]=[C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[C:10]2[C:21](=[O:24])[NH:22][CH2:23][C:9]=2[CH:8]=1.[B-](F)(F)(F)[F:34].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(Cl)Cl.CCOC(C)=O.C1COCC1.CCOC(C)=O>[F:34][C:8]1[C:9]2[CH2:23][NH:22][C:21](=[O:24])[C:10]=2[C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[N:12][C:7]=1[NH:6][CH2:5][C@@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:3][O:2][CH3:1]

参加物

6

反応物 2

HCID 2724933SelectfluorHCID 67238901(R)-tert-Butyl 1-methoxy-3-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)propan-2-ylcarbamate

生成物 1

HCID 67238798(R)-tert-Butyl 1-(7-fluoro-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-3-methoxypropan-2-ylcarbamate

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 21939870Tetrahydrofuran ethyl acetate溶媒

反応条件

温度
0 °C

実験手順

To a screw-top vial was added (R)-tert-butyl 1-methoxy-3-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)propan-2-ylcarbamate (27 mg, 0.061 mmol) in a mixture of DCM and MeOH (1/1, 1.2 mL). The resulting colorless solution was cooled to 0° C. SELECTFLUOR® (21.66 mg, 0.061 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. Next, the reaction mixture was diluted with EtOAc (10 mL) and washed with saturated aq sodium bicarbonate (5 mL), water (5 mL), and brine (5 mL). The organic layer was collected, dried over Na2SO4, and concentrated to give the title compound as a brown residue, which was used without further purification (32 mg, 114%). [M+H] calc'd for C23H30FN5O4, 460. found, 460.

後処理

  1. washwashed with saturated aq sodium bicarbonate (5 mL), water (5 mL), and brine (5 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-70a41c196b3b45fd9b483793f845df6d
出典データセット
uspto-grants-2013_05
特許番号
US08440689B2

反応ノート

読み込み中…