Diisopropylethylamine → HCID 60204370, compound

HRID 2267321Notes

Reaction equation

HRID 2267321 reaction equation
[Br:1][C:2]1[C:3]([C:12]2[S:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[N:20]=2)=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[NH2:21][CH2:22][CH2:23][N:24]1[C:28]([CH3:30])([CH3:29])[C:27](=[O:31])[NH:26][C:25]1=[O:32].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Br:1][C:2]1[C:3]([C:12]2[S:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[N:20]=2)=[N:4][C:5]([NH:21][CH2:22][CH2:23][N:24]2[C:28]([CH3:29])([CH3:30])[C:27](=[O:31])[NH:26][C:25]2=[O:32])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dioneHCID 602043722-(5-Bromo-2-(methylsulfonyl)pyrimidin-4-yl)thiazolo[5,4-c]pyridine

Product 1

HCID 60204370HCID 60204370, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
160 °C

Procedure

A microwave tube was charged with 2-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)thiazolo[5,4-c]pyridine (300 mg, 0.81 mmol), 1-(2-Aminoethyl)-5,5-dimethyl-imidazolidine-2,4-dione (138 mg, 0.81 mmol), isopropanol (3 mL) and N,N-diisopropylethylamine (0.21 mL, 1.21 mmol). The vessel was sealed and heated in a microwave reactor at 160° C. for 1000 seconds. The resulting solid was filtered off and washed with methanol (4×10 mL). The solid was then dissolved in dimethylsulfoxide (4 mL) and purified by reverse phase HPLC. Product fractions were combined and loaded onto an SCX cartridge, washed with methanol (4 mL), then free based and eluted with 2 M ammonia in methanol (4 mL). The solvent was evaporated in vacuo to yield 1-(2-(5-bromo-4-(thiazolo[5,4-c]pyridin-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (17 mg, 5%) as a yellow amorphous solid. 1H NMR 6 (d6-DMSO, 400 MHz) 1.50 (s, 6 H), 3.67 (br. s., 2 H), 3.75 (br. s., 2 H), 4.32 (br. s., 1 H), 6.89 (s, 1 H), 7.49 (s, 1 H), 8.33 (d, J=5.5 Hz, 1 H), 8.91 (d, J=5.1 Hz, 1 H), 9.71 (s, 1 H): HRMS (M+H)+ Calcd. C17H16BrN7O2S 462.0348, found 462.0339.

Workup

  1. customThe vessel was sealed
  2. filtrationThe resulting solid was filtered off
  3. washwashed with methanol (4×10 mL)
  4. dissolutionThe solid was then dissolved in dimethylsulfoxide (4 mL)
  5. custompurified by reverse phase HPLC
  6. washwashed with methanol (4 mL)
  7. washeluted with 2 M ammonia in methanol (4 mL)
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d4b45daec7c0449cb09497deef58e910
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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