Water → HCID 67620600, compound

HRID 1418039Notes

Reaction equation

HRID 1418039 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22](C2CCCCO2)[CH:21]=[CH:20]3)[S:13][C:14]=1[CH3:15].[H-].[Na+].[CH2:34](Br)[CH2:35][CH3:36].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]([N:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)[CH2:34][CH2:35][CH3:36])[S:13][C:14]=1[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 88328820HCID 88328820, compound

Product 1

HCID 67620600HCID 67620600, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.9 g of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(1-(tetrahydropyran-2-yl)indol-5-yl)amino]-thiazole are dissolved in 110 ml of dimethylformamide. 1.06 g of 60% sodium hydride in oil and then 3.2 ml of propyl bromide are added at 0° C. After stirring for 16 hours at room temperature, the reaction mixture is poured onto 500 ml of water and extracted 3 times with 250 ml ethyl acetate. The organic phase is washed with 3 times 200 ml of water, dried over sodium sulphate and evaporated to dryness. The residue is purified by flash chromatography on silica gel eluted with a 3/1 (v/v) cyclohexane/ethyl acetate mixture. 10.17 g of the expected product (85%) are obtained. 1H NMR (CDCl3): 0.90 (m, 3H), 1.57-1.75 (m, 6H), 2.02 (s, 3H), 1.95-2.25 (m, 2H), 3.70-4.17 (m, 7H), 5.50 (dd, J=2.6, 10.0, 1H), 6.54-7.61 (m, 8H).

Workup

  1. extractionextracted 3 times with 250 ml ethyl acetate
  2. washThe organic phase is washed with 3 times 200 ml of water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness
  5. customThe residue is purified by flash chromatography on silica gel
  6. washeluted with a 3/1 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-02ec044f41d8425e9dcdc94bd48ad41f
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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