Sodium triacetoxyborohydride → 4-methyl-5-(1-(4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)propan-2-yl)isobenzofuran-1(3H)-one

HRID 1519649노트

반응식

HRID 1519649 반응식
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]([CH3:20])[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH3:21][C:22]1[C:30]2[CH2:29][O:28][C:27](=[O:31])[C:26]=2[CH:25]=[CH:24][C:23]=1[CH2:32][CH:33]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:1][C:2]1[C:3]([CH:12]([CH3:20])[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:33][CH2:32][C:23]3[C:22]([CH3:21])=[C:30]4[C:26](=[CH:25][CH:24]=3)[C:27](=[O:31])[O:28][CH2:29]4)[CH2:16][CH2:15]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[CH2:9][O:8][C:7]2=[O:11]

참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 595686964-Methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-oneHCID 772312602-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

생성물 1

HCID 569710914-methyl-5-(1-(4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)propan-2-yl)isobenzofuran-1(3H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 12 mL reaction vial was added 4-methyl-5-[1-(piperazine-1-yl)propan-2-yl]-2-benzofuran-1(3H)-one (57 mg, 0.208 mmol), (4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (47.4 mg, 0.25 mmol) and dichloromethane (5 mL). The solution was stirred at RT under N2 for 10 min. To above solution was added NaB(OAc)3H (88 mg, 0.42 mmol). The reaction was stirred at RT for 18 hours under N2, extracted with DCM, washed with brine and water. The organic phase was dried over MgSO4, filtered and purified by flash column chromatography to give desired product. LC-MS (IE, m/z): 449.4 [M+1]+. 1H NMR (500 MHz, CDCl3, δ in ppm): 7.73 (1H, d, J=8.0 Hz), 7.67 (1H, d, J=8.0 Hz), 7.40 (1H, d, J=8.0 Hz), 7.32 (1H, d, J=8.0 Hz), 5.25 (2H, s), 5.23 (2H, s), 3.33 (1H, q), 2.90 (2H, m), 2.4-2.6 (12H, m), 2.30 (3H, s), 2.27 (3H, s), 1.28 (3H, d, J=6.6 Hz). (0.034 μM)

후처리

  1. customTo a 12 mL reaction
  2. stirringThe reaction was stirred at RT for 18 hours under N2
  3. extractionextracted with DCM
  4. washwashed with brine and water
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. custompurified by flash column chromatography

출처 및 근거

ORD 기록
ord-ffe0eb373f0847da95f6059c1342a4c6
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073882B2

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