Ethanolamine → HCID 69665754, compound

HRID 1064314Notes

Reaction equation

HRID 1064314 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.[CH2:27]([CH2:29][NH2:30])[OH:28]>S(Cl)(Cl)=O.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:30][CH2:29][CH2:27][OH:28])=[CH:9][CH:8]=3)[N:18]=2)=[CH:20][N:21]=[C:22]1[CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 24638Chlorosulfonic acidHCID 22273557HCID 22273557, compound

Product 1

HCID 69665754HCID 69665754, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulphonic acid (150 μL, 2.16 mmol) was added dropwise to 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 at 0° C. and the mixture stirred at 0° C. for 10 minutes then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the residue was dried under high vacuum (<2 mmHg) for 1 hour. The resulting solid was placed under nitrogen and a solution of ethanolamine (494 mg, 8.1 mmol) in MeOH (3 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. Water (20 ml) was added and the precipitated solid was collected by filtration, washed with water (2×10 ml) and ether (2×10 ml) and and dried under vacuum at 60° C. to yield the title compound (177 mg, 81%) as a beige solid. NMR 1.22 (t, 3H), 2.41 (s, 3H), 2.80 (s, 2H), 3.38 (q, 2H), 4.63 (m, 3H), 7.20 (d, 1H), 7.36 (s, 1H), 7.77 (s, 1H), 7.82 (d, 2H), 7.91 (d, 2H), 8.34 (d, 1H), 9.85, (s, 1H); m/z 403.

Workup

  1. temperaturethen heated at 90° C. for 90 minutes
  2. customThe volatiles were removed by evaporation
  3. customthe residue was dried under high vacuum (<2 mmHg) for 1 hour
  4. stirringThe mixture was stirred for 30 minutes
  5. customthe volatiles were evaporated in vacuo
  6. additionWater (20 ml) was added
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed with water (2×10 ml) and ether (2×10 ml)
  9. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-b8b09309bfa748cdac8353f67cef5709
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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