Dimethyl Sulfate → HCID 11531359, compound

HRID 2092182Notes

Reaction equation

HRID 2092182 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([NH:16][C:17]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[N:23][NH:24]4)=[O:18])[CH2:7][C:8]([CH2:14][CH3:15])([CH2:12][CH3:13])[O:9]2)=[CH:4][CH:3]=1.[H-].[Na+].S(OC)(O[CH3:35])(=O)=O>CN(C)C=O>[CH2:12]([C:8]1([CH2:14][CH3:15])[CH2:7][CH:6]([NH:16][C:17]([NH:19][C:20]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=2[CH:22]=[N:23][N:24]3[CH3:35])=[O:18])[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[O:9]1)[CH3:13]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 11516487HCID 11516487, compound

Product 1

HCID 11531359HCID 11531359, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 77D (212 mg, 0.554 mmol) in N,N-dimethylformamide (2.2 mL) was treated with 60% NaH (28 mg, 0.7 mmol), and the mixture was stirred at rt for 45 min. Dimethyl sulfate (0.06 mL, 0.634 mmol) was then added, and the reaction was allowed to stir for 1 h. Concentration in vacuo, followed by silica gel chromatography (98:2 dichloromethane-methanol, eluent) afforded the title compound as a tan foamy solid, 109 mg (50%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.72 (s, 1H), 8.03 (s, 1H), 7.70 (d, J=7.1 Hz, 1H), 7.25-7.36 (m, 2H), 7.17 (m, 1H), 6.70-6.77 (m, 2H), 6.63 (dd, J=10.5, 2.7 Hz, 1H), 4.94 (m, 1H), 4.00 (s, 3H), 2.19 (m, 1H), 1.58-1.77 (m, 5H), 0.84-0.94 (m, 6H). MS (ESI) m/z 397 (M+H).

Workup

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

Sources & evidence

ORD record
ord-c0ba9a51b6af47ea92d128e101c66026
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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