1,2-Dimethoxyethane → HCID 53324534, compound

HRID 2110637Notes

Reaction equation

HRID 2110637 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH:6]=[C:5]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:4]=1.S([CH2:38][N+:39]#[C-:40])(C1C=CC(C)=CC=1)(=O)=O.COCCOC>O>[CH3:1][O:2][C:3]1[N:4]=[C:5]([NH:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH:6]=[C:7]([C:9]2[CH:16]=[CH:15][CH:14]=[C:11]([C:12]3[O:13][CH:40]=[N:39][CH:38]=3)[CH:10]=2)[N:8]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 161915Tosylmethyl isocyanideHCID 57636122HCID 57636122, compound

Product 1

HCID 53324534HCID 53324534, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In a tube is combined 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde (200 mg, 0.55 mmol), tosylmethylisocyanide (119 mg, 0.61 mmol), Ambersep 900 OH resin (1 g), ethylene glycol dimethyl ether (3.5 mL) and water (3.5 mL). The tube is sealed and the mixture is heated to 85° C. and stirred for 18 hours. The mixture is allowed to cool to ambient temperature and filtered to remove the resin, and washed the resin with 10 mL methanol. The combined filtrate and washings are concentrated by rotary evaporator and the residue is subjected to flash column chromatography on silica gel eluting with 10 to 40% EtOAc in heptane gradient, to afford [2-methoxy-6-(3-oxazol-5-yl-phenyl)-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine [65 mg, 29.4%, Example 11(b)]. LCMS: RT=2.59 minutes MS: 403 (M+H). IC50=2.6 nM

Workup

  1. customIn a tube is combined
  2. customThe tube is sealed
  3. temperatureto cool to ambient temperature
  4. filtrationfiltered
  5. customto remove the resin
  6. washwashed the resin with 10 mL methanol
  7. concentrationThe combined filtrate and washings are concentrated by rotary evaporator

Sources & evidence

ORD record
ord-132098181d044a86b999dfd77649b3d4
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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