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Formaldehyde → 2-[(1-Methylethyl)oxy]-5-[3-(2-methyl-1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile

HRID 2059949
ノート
印刷プレビュー

反応式

HRID 2059949 の反応式
[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][NH:22][CH2:23]4)[N:14]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:32](C)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O.CS(C)=O.CO>[CH3:3][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][N:22]([CH3:32])[CH2:23]4)[N:14]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:1]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 441248992-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile

生成物 1

HCID 441250302-[(1-Methylethyl)oxy]-5-[3-(2-methyl-1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile収率 78%

試薬・触媒・溶媒 3

HCID 6344
Dichloromethane
溶媒
HCID 22036561Dimethyl sulfoxide methanol溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 2-[(1-methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile (Example 3, 25.0 mg, 0.069 mmol) and formaldehyde (37% w/v in H2O, 8.0 μL, 0.10 mmol) in DCM (5 mL) was added NaBH(OAc)3 (29 mg, 0.14 mmol) and the resulting solution stirred at room temperature for 20 min. Brine (5 mL) was added, and the aqueous extracted with DCM (5 mL). The combined organics were concentrated in vacuo to give a white solid. This solid was redissolved in DMSO-MeOH, added to an SCX cartridge and washed with MeOH. The product was eluted with NH3 in MeOH; concentration in vacuo gave a white solid (20.1 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 8.41 (1H, d), 8.32 (1H, dd), 7.98 (1H, d), 7.29 (1H, t), 7.20 (1H, d), 7.12 (1H, d), 4.79 (1H, sept), 3.67 (2H, s), 3.30 (2H, t), 2.75 (2H, t), 2.49 (3H, s), 1.47 (6H, d).

後処理

  1. extractionthe aqueous extracted with DCM (5 mL)
  2. concentrationThe combined organics were concentrated in vacuo
  3. customto give a white solid
  4. additionadded to an SCX cartridge
  5. washwashed with MeOH
  6. washThe product was eluted with NH3 in MeOH
  7. concentrationconcentration in vacuo

出典と根拠

ORDレコード
ord-62868c038b884a5a88a06bacb91c2e35
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08278324B2

反応ノート

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