Dimethyl Sulfate → HCID 24804625, compound

HRID 1908696Notes

Reaction equation

HRID 1908696 reaction equation
[F:1][C:2]1[CH:14]=[C:13]2[C:5]([CH:6]([NH:15][C:16]([NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH:21]=[N:22][NH:23]4)=[O:17])[CH2:7][C:8]3([O:12]2)[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=1.[H-].[Na+].S(OC)(O[CH3:34])(=O)=O>CN(C)C=O>[F:1][C:2]1[CH:14]=[C:13]2[C:5]([CH:6]([NH:15][C:16]([NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH:21]=[N:22][N:23]4[CH3:34])=[O:17])[CH2:7][C:8]3([O:12]2)[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 24804471HCID 24804471, compound

Product 1

HCID 24804625HCID 24804625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 3D (483 mg, 1.32 mmol) in N,N-dimethylformamide (5 mL) was treated with 60% NaH (65 mg, 1.63 mmol), and the mixture was stirred at room temperature for 45 min. Dimethyl sulfate (0.14 mL, 1.48 mmol) was then added, and the reaction was allowed to stir for 1 h. Concentration in vacuo, followed by silica gel chromatography (98:2 CH2Cl2-methanol, eluent), afforded the title compound as an off-white solid, 121 mg (24%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.74 (s, 1H), 8.03 (s, 1H), 7.72 (d, J=7.1 Hz, 1H), 7.29 (m, 2H), 7.16 (d, J=8.5 Hz, 1H), 6.77 (m, 2H), 6.66 (dd; J=10.5, 7.8 Hz; 1H), 4.97 (m, 1H), 4.01 (s, 3H), 2.40 (m, 1H), 2.12-2.30 (m, 4H), 1.65-1.99 (m, 3H). MS (ESI+) m/z 381 (M+H).

Workup

  1. stirringto stir for 1 h
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-087fe42fa19e430a8e9c126b8305336b
Source dataset
uspto-grants-2013_12
Patent number
US08598220B2

Reaction notes

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