Toluene → 8-Fluoro-N-methoxy-N-methyl-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]-benzoxazine-2-carboxamide

HRID 1867253ノート

反応式

HRID 1867253 の反応式
Cl.[CH3:2][NH:3][O:4][CH3:5].C[Al](C)C.[F:10][C:11]1[CH:12]=[CH:13][C:14]2[O:19][CH2:18][CH:17]3[CH:20](C4C=CC=CC=4)[CH:21]=[N:22][N:16]3[C:15]=2[CH:29]=1.CCC([O-])=[O:33].[C:35]1([CH3:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[F:10][C:11]1[CH:12]=[CH:13][C:14]2[O:19][CH2:18][CH:17]3[CH:41]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:21]([C:20]([N:3]([O:4][CH3:5])[CH3:2])=[O:33])=[N:22][N:16]3[C:15]=2[CH:29]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 16682925TrimethylaluminumHCID 866247908-Fluoro-3-phenyl-3a,4-dihydro-3H-pyrazolo(5,1-c)(1,4)benzoxazine 2-ethylcarboxylate

生成物 1

HCID 730455398-Fluoro-N-methoxy-N-methyl-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]-benzoxazine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A suspension of N-methylmethoxyamine hydrochloride (0.048 g, 0.485 mmol) in dichloromethane (6 mL) at 0° C. was treated with a solution of trimethylaluminum (0.48 mL of a 2.0 M soln in PhMe, 0.971 mmol) and stirred for 20 min. A solution of racemic ester (1-6) (0.150 g, 0.441 mmol) in dichloromethane (2 mL) was added. After stirring for 48 h, the reaction was quenched by the addition of satd. aq. NH4Cl and extracted with EtOAc (2×50 mL). The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2, 25% EtOAc/hexanes) to provide desired amide (1-7) as a racemic mixture. 1HNMR (500 MHz, CDCl3) δ 7.33-7.35 (m, 4H), 7.17 (m, 1H), 7.10 (m, 1H), 6.80-6.77 (m, 1H), 6.54 (m, 1H), 4.98 (d, J=12.2 Hz, 1H), 4.38 (m, 1H), 3.86-3.82 (m, 4H), 3.30 (br s, 1H) 2.04 (s, 3H) ppm.

後処理

  1. stirringAfter stirring for 48 h
  2. customthe reaction was quenched by the addition of satd
  3. extractionaq. NH4Cl and extracted with EtOAc (2×50 mL)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, 25% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-5a9ad0b06a554460bcbbbc36f0527dba
出典データセット
uspto-grants-2009_12
特許番号
US07632833B2

反応ノート

読み込み中…