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

HRID 1867253노트

반응식

HRID 1867253 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5a9ad0b06a554460bcbbbc36f0527dba
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632833B2

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