Diethylmethylamine → HCID 22273523, compound

HRID 1064315Notes

Reaction equation

HRID 1064315 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH2:24][CH3:25])[C:22]([CH3:26])=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.NCC[CH2:30][CH2:31][OH:32].[CH2:33]([N:35](CC)C)[CH3:34].S(Cl)(Cl)=[O:40]>CO>[CH2:24]([N:23]1[C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([S:2](=[O:5])(=[O:3])[NH:35][CH2:33][CH2:34][O:40][CH2:30][CH2:31][OH:32])=[CH:9][CH:8]=3)[N:18]=2)=[CH:20][N:21]=[C:22]1[CH3:26])[CH3:25]

Participants

7

Reactant 5

HCID 12022DiethylmethylamineHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 258684-Amino-1-butanolHCID 22273557HCID 22273557, compound

Product 1

HCID 22273523HCID 22273523, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to a solution of 2-anilino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine (Example 28; 150 mg, 0.54 mmol) in thionyl chloride (3 ml) cooled to 0° C. and the mixture stirred for 10 minutes at 0° C. then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the resultant solid placed under high vacuum (<2 mmHg) for 1 hr. The resulting solid was placed under nitrogen and a solution of 2-(2-aminoethyl)ethanol (114 mg, 1.00 mmol) and diethylmethylamine in MeOH (3 ml) was cautiously added. The solution was stirred for 30 minutes and the volatiles were evaporated. Water (20 ml) was added and the precipitated solid was collected by filtration and washed with water (2×10 ml). The residue was dissolved in MeOH (5 ml) and loaded on to an Isolute amine column, eluted with MeOH (30 ml) and the fractions containing product were evaporated to give the title compound (190 mg, 79%) as a beige solid. NMR 1.18 (t, 3H), 2.39 (s, 3H), 2.89 (t, 2H), 3.15 (m, 7H), 4.38 (q, 2H), 7.21 (d, 1H), 7.71 (m, 3H), 7.89 (d, 2H), 8.41 (d, 1H), 9.82 (s, 1H); m/z 447.

Workup

  1. temperaturethen heated at 90° C. for 90 minutes
  2. customThe volatiles were removed by evaporation
  3. waitthe resultant solid placed under high vacuum (<2 mmHg) for 1 hr
  4. stirringThe solution was stirred for 30 minutes
  5. customthe volatiles were evaporated
  6. additionWater (20 ml) was added
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed with water (2×10 ml)
  9. dissolutionThe residue was dissolved in MeOH (5 ml)
  10. washeluted with MeOH (30 ml)
  11. additionthe fractions containing product
  12. customwere evaporated

Sources & evidence

ORD record
ord-e8bfac32f8564dd0aaaf6c8950cb0a15
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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