Methyl iodide → HCID 56665092, compound

HRID 1519813Notes

Reaction equation

HRID 1519813 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([C:24]2[N:28]=[CH:27][NH:26][N:25]=2)=[C:6]([NH:9][C:10](=[O:23])[CH2:11][N:12]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:13]2=[O:22])[S:7][CH:8]=1.I[CH3:30]>CN(C=O)C.O>[Br:3][C:4]1[C:5]([C:24]2[N:28]=[CH:27][N:26]([CH3:30])[N:25]=2)=[C:6]([NH:9][C:10](=[O:23])[CH2:11][N:12]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:13]2=[O:22])[S:7][CH:8]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178521250HCID 178521250, compound

Product 1

HCID 56665092HCID 56665092, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (4.2 mg of a 60% dispersion in mineral oil, 0.107 mmol) was added to a solution of N-(4-bromo-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide (31 mg, 0.0715 mmol) in DMF (0.1 mL) at 0° C. The suspension was stirred for 5 minutes after which iodomethane (12 mg, 0.058 mmol) was added. The reaction mixture was stirred at room temperature for 20 minutes then diluted with water, extracted with ethyl acetate, dried (Na2SO4), filtered, concentrated under vacuum and purified by preparative HPLC to give N-(4-bromo-3-(1-methyl-1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide. Retention time (min)=1.740, method [7], MS(ESI) 447.0 (M+H); 1H NMR (300 MHz, CD3OD) δ 8.47 (s, 1H), 8.33 (d, J=5.2 Hz, 1H), 7.85 (bs, 1H), 7.61 (bs, 1H), 7.11 (s, 1H), 4.94 (s, 2H), 4.02 (s, 3H), 3.41-3.36 (m, 2H), 3.01-2.97 (m, 2H).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d9cfaa75f95348c5a234655f4490d4ff
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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