Methyl iodide → HCID 178466940, compound

HRID 1295456Notes

Reaction equation

HRID 1295456 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[C:15]3[S:19][C:18](=S)[NH:17][C:16]3=[O:21])[CH:12]=2)[N:7]=[C:6]([NH:22][C:23](=[O:25])[CH3:24])[CH:5]=1)[CH3:2].C(N(C(C)C)CC)(C)C.CI.[NH2:37][CH2:38][CH2:39][CH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>C(#N)C>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[C:15]3[S:19][C:18]([NH:37][CH2:38][CH2:39][CH:40]4[CH2:45][CH2:44][O:43][CH2:42][CH2:41]4)=[N:17][C:16]3=[O:21])[CH:12]=2)[N:7]=[C:6]([NH:22][C:23](=[O:25])[CH3:24])[CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 81531Diisopropylethylamine2×HCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 178466942HCID 178466942, compound

Product 1

HCID 178466940HCID 178466940, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of N-[4-ethoxy-6-(4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-quinolin-2-yl]-acetamide (example 6a, 50 mg, 0.11 mmol) in acetonitrile (1.5 ml) was reacted with diisopropylethyl amine (0.200 ml, 1.15 mmol) and methyl iodide (0.15 ml, 2.3 mmol) at rt for 30 min. The mixture was concentrated to dryness and the residue suspended in acetonitrile (1.5 ml). Diisopropylethyl amine (0.20 ml, 1.15 mmol) and 4-(2-aminoethyl)tetrahydropyran (0.075 ml, 0.58 mmol) were successively added at rt, and the mixture was stirred at rt overnight. The precipitate was collected by suction filtration, an washed with acetronitrile. It was then absorbed on SiO2 and purified on a silica gel column with a 0–10% methanol/ethyl acetate gradient to afford the product N-(4-ethoxy-6-{4-oxo-2[2-(tetrahydro-pyran-4-yl)-ethylamino]-4H-thiazol-5-ylidenemethyl}-quinolin-2-yl)-acetamide as a pale yellow solid (22 mg, 50%). LC-MS m/e 469 (MH+).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. filtrationThe precipitate was collected by suction filtration
  3. washan washed with acetronitrile
  4. customIt was then absorbed on SiO2
  5. custompurified on a silica gel column with a 0–10% methanol/ethyl acetate gradient

Sources & evidence

ORD record
ord-c04cdf44e8354676a9ddfa4929f2d1c3
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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