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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
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HRID 2059949 반응식
[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]
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 6344
Dichloromethane
용매
HCID 22036561Dimethyl sulfoxide methanol용매
HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-62868c038b884a5a88a06bacb91c2e35
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08278324B2

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