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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
Notes
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Reaction equation

HRID 2059949 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6344
Dichloromethane
Solvent
HCID 22036561Dimethyl sulfoxide methanolSolvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-62868c038b884a5a88a06bacb91c2e35
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08278324B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes