Dimethylformamide → HCID 66747714, compound

HRID 2402146Notes

Reaction equation

HRID 2402146 reaction equation
[C:1]([C:3]1[C:4]([CH:17]([OH:28])[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=C(C(O)=O)[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].[CH3:29]N(C)C=O.CI.C[CH2:37][O:38][C:39]([CH3:41])=[O:40]>[Ag-]=O>[C:1]([C:3]1[C:4]([CH:17]([O:28][CH3:29])[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[C:41]([C:39]([O:38][CH3:37])=[O:40])[S:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)#[N:2]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 68006687HCID 68006687, compound

Product 1

HCID 66747714HCID 66747714, compound

Reagents, catalysts & solvents 1

HCID 178418778HCID 178418778, compoundCatalyst

Procedure

To a round bottom flask was added silver(I) oxide (56.15 g, 0.2423 mol), 4-cyano-3-[hydroxy(2-naphthyl)methyl]-5-(morpholin-4-yl)thiophene-2-carboxylic acid (15.17 g, 0.02423 mol), and N,N-dimethylformamide (66.2 mL), followed by methyl iodide (53.7 mL, 0.863 mol). Added another 10 mL DMF, sonicated to suspend/mix all solid. The reaction mixture was stirred at room temperature for 26 hours, then was diluted with EtOAc, filtered through a pad of Celite, concentrated filtrate in vacuo, azeotroped w/toluene (10×10 mL), DCM (20 mL), dried on high vacuum pump. The rude material was used directly in the next step. LC/MS (AA) ES+ 423, ES+Na+445; 1H NMR (400 MHz, DMSO) δ 7.97 (s, 1H), 7.91-7.86 (m, 3H), 7.53-7.48 (m, 3H), 6.62 (s, 1H), 3.85 (s, 3H), 3.72-3.69 (m, 4H), 3.52-3.50 (m, 4H), 3.43 (s, 3H).

Workup

  1. customsonicated
  2. additionto suspend/mix all solid
  3. filtrationfiltered through a pad of Celite, concentrated filtrate in vacuo
  4. customazeotroped w/toluene (10×10 mL), DCM (20 mL)
  5. customdried on high vacuum pump

Sources & evidence

ORD record
ord-398c0c89f7414287ae969ac60ba1637a
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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