Methyl iodide → HCID 59619993, compound

HRID 445709Notes

Reaction equation

HRID 445709 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[C:19]3[C:18]4[CH:17]=[C:16]([C:20]5[CH:21]=[N:22][C:23]([CH2:29][OH:30])=[C:24]([NH:26][CH2:27][CH3:28])[CH:25]=5)[CH:15]=[CH:14][C:13]=4[N:12]=[CH:11][C:10]=3[N:9]([CH3:31])[C:8]2=[O:32])[C:4]([CH3:33])=[N:3]1.[H-].[Na+].I[CH3:37]>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[C:19]3[C:18]4[CH:17]=[C:16]([C:20]5[CH:21]=[N:22][C:23]([CH2:29][O:30][CH3:37])=[C:24]([NH:26][CH2:27][CH3:28])[CH:25]=5)[CH:15]=[CH:14][C:13]=4[N:12]=[CH:11][C:10]=3[N:9]([CH3:31])[C:8]2=[O:32])[C:4]([CH3:33])=[N:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 49834899HCID 49834899, compound

Product 1

HCID 59619993HCID 59619993, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(1,3-dimethyl-1H-pyrazol-4-yl)-8-(5-ethylamino-6-hydroxymethyl-pyridin-3-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Example 155.1, 0.086 mmol) in DMF (0.5 ml) was treated with 55% NaH in oil (0.086 mmol) and the RM was stirred for 10 min at rt, then was added iodomethane (0.086 mmol) and the RM was stirred for 2 h at rt. The RM was quenched with water, diluted with DMF, filtered and purified by preparative HPLC. The pure fractions were basified with NaHCO3, concentrated and extracted with CH2Cl2 (3×) and with EtOAc. The combined organic layers were dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a film. (HPLC: tR 2.24 min (Method A); M+H=458 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.13-8.08 (m, 2H), 7.98-7.91 (m, 2H), 7.64-7.61 (m, 1H), 6.90 (s, 1H), 5.32 (t, 1H), 4.53 (s, 2H), 3.88 (s, 3H), 3.58 (s, 3H), 3.28 (s, 3H), 3.20 (qt, 2H), 1.97 (s, 3H), 1.23 (t, 3H))

Workup

  1. stirringthe RM was stirred for 2 h at rt
  2. customThe RM was quenched with water
  3. additiondiluted with DMF
  4. filtrationfiltered
  5. custompurified by preparative HPLC
  6. concentrationconcentrated
  7. extractionextracted with CH2Cl2 (3×) and with EtOAc
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-bd87b6ecc9d242ad8d5825167c155b70
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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