Acetic Acid → HCID 117599462, compound

HRID 1466161Notes

Reaction equation

HRID 1466161 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][CH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.[BH3-]C#N.[Na+].CC(O)=O.[O:28]=[C:29]1[C:33]2[CH:34]=[CH:35][C:36]([CH2:38][CH:39]=O)=[CH:37][C:32]=2[CH2:31][O:30]1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][N:6]([CH2:39][CH2:38][C:36]2[CH:35]=[CH:34][C:33]3[C:29](=[O:28])[O:30][CH2:31][C:32]=3[CH:37]=2)[CH2:5][CH2:4][N:3]1[CH2:8][CH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 89526020HCID 89526020, compound

Product 1

HCID 117599462HCID 117599462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-[(2-Oxopiperazin-1-yl)methyl]-2,3-dihydro-1H-indene-5-carbonitrile (42 mg, 0.16 mmol), NaBH3CN (40 mg, 0.66 mmol) and HOAc (40 mg, 0.66 mmol) in 20 mL DCM was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (29 mg, 0.16 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 title product. 1H-NMR (400 MHz, CDCl3) δ ppm 7.84 (d, J=8.6 Hz, 2H), 7.50 (s, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.32 (s, 1H), 7.27 (d, J=7.8 Hz, 1H), 5.28 (s, 2H), 3.50˜3.61 (m, 3H), 3.20˜3.32 (m, 4H), 2.99˜3.08 (m, 1H), 2.84˜2.95 (m, 3H), 2.67˜2.77 (m, 4H), 2.21˜2.30 (m, 1H), 1.87˜1.95 (m, 1H).

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-d8d5549261294bb4811e7aa5fe5f830f
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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