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 1519649ノート

反応式

HRID 1519649 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-ffe0eb373f0847da95f6059c1342a4c6
出典データセット
uspto-grants-2015_07
特許番号
US09073882B2

反応ノート

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