Acetic Acid → HCID 89533488, compound

HRID 1466154Notes

Reaction equation

HRID 1466154 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:19]#[N:20])[CH:12]=[CH:11][C:10]1=2.[BH3-]C#N.[Na+].CC(O)=O.[O:29]=[C:30]1[C:34]2[CH:35]=[CH:36][C:37]([CH2:39][CH:40]=O)=[CH:38][C:33]=2[CH2:32][O:31]1.C([O-])([O-])=O.[Na+].[Na+]>CO>[O:1]=[C:2]1[CH2:7][N:6]([CH2:40][CH2:39][C:37]2[CH:36]=[CH:35][C:34]3[C:30](=[O:29])[O:31][CH2:32][C:33]=3[CH:38]=2)[CH2:5][CH2:4][N:3]1[CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:19]#[N:20])[CH:12]=[CH:11][C:10]1=2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 89525041HCID 89525041, compound

Product 1

HCID 89533488HCID 89533488, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-[(2-Oxopiperazin-1-yl)methyl]-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (40 mg, 0.15 mmol), NaBH3CN (19 mg, 0.30 mmol) and HOAc (18 mg, 0.298 mmol) in 20 mL MeOH was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (52 mg, 0.30 mmol) and the mixture was stirred at RT overnight. Then saturated Na2CO3 (50 mL) was added and stirred for 30 min and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by prep-TLC to give the desired product. 1H-NMR (400 MHz, MeOD) δ ppm 7.78 (d, J=7.8 Hz, 1H), 7.39˜7.51 (m, 4H), 7.31 (d, J=7.8 Hz, 1H), 5.34 (s, 2H), 3.74˜3.80 (m, 1H), 3.32˜3.43 (m, 3H), 3.25˜3.28 (m, 1H), 3.21 (s, 2H), 2.97˜3.01 (m, 2H), 2.74˜2.84 (m, 6H), 1.89˜1.96 (m, 1H), 1.71˜1.79 (m, 3H).

Workup

  1. stirringstirred for 30 min
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-e091828b1b7441e693f4654b459949aa
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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