Dimethylformamide → HCID 53916846, compound

HRID 1416617Notes

Reaction equation

HRID 1416617 reaction equation
Cl.Cl.[C:3]([CH2:5][C@H:6]1[CH2:10][N:9]([CH3:11])[C@H:8]([CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:7]1)#[N:4].CN(C=O)C.[C-]#N.[Na+]>O>[C:3]([CH2:5][C@H:6]1[CH2:10][N:9]([CH3:11])[C@H:8]([CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:7]1)#[N:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 67586082HCID 67586082, compound

Product 1

HCID 53916846HCID 53916846, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A 132 mg sample of the compound from step 50a above was dissolved 4 mL of a 6:1 solution of DMF:H2O, 240 mg of NaCN was added, and the reaction mixture was stirred at 95° C. for 16 hours. The solvent was removed, and the residue was purified by column chromatography on silica gel, eluting with 10:1 chloroform:methanol to afford 62 mg of the title compound. MS (DCI/NH3) m/e: 232 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.34 (m, 1H), 8.28 (m, 1H); 7.30-7.20 (m, 2H), 4.28-4.06 (m, 2H), 3.05-2.72 (m, 5H), 2.65-2.52 (br s, 3H), 2.42-2.25 (m, 1H), 2.23-2.0 (m, 2H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography on silica gel
  3. washeluting with 10:1 chloroform

Sources & evidence

ORD record
ord-bfafeaee1570413e95154fc7da7baff2
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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