Dimethyl Sulfate → HCID 24804625, compound

HRID 1437495Notes

Reaction equation

HRID 1437495 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-5df6942bf2604f3298313cfb59553200
Source dataset
uspto-grants-2009_11
Patent number
US07622493B2

Reaction notes

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