Triethylamine → HCID 68685040, compound

HRID 1441330Notes

Reaction equation

HRID 1441330 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:18]=[C:17]([C:19]4[N:23]([CH:24]([CH3:26])[CH3:25])[C:22]([CH3:27])=[N:21][CH:20]=4)[C:16]([F:28])=[CH:15][N:14]=3)=[CH:8][CH:7]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[F:28][C:16]1[C:17]([C:19]2[N:23]([CH:24]([CH3:25])[CH3:26])[C:22]([CH3:27])=[N:21][CH:20]=2)=[N:18][C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([N:4]3[CH2:3][CH:2]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:5]3)=[CH:11][CH:10]=2)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68686065HCID 68686065, compound

Product 1

HCID 68685040HCID 68685040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[4-(3-aminoazetidin-1-yl)phenyl]-5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-amine (Example 140; 110 mg, 0.29 mM) and triethylamine (44 μl, 0.317 mM) in dry DCM (4.0 ml), methanesulphonyl chloride (25 μl, 0.317 mM) was added. The reaction was stirred at room temperature under nitrogen for 24 hours. The reaction was filtered and the filtered solid washed with DCM. This solid which was pure product was retained. The filtrate was taken and more DCM added. The solution was washed in turn with water (twice), saturated sodium chloride and then dried with anhydrous sodium sulphate, filtered and evaporated. The product so obtained was combined with the 1st batch of product and both were triturated with ether, filtered, washed with ether and dried to give the title compound as a yellow solid. NMR 1.4 (d, 6H), 2.6 (s, 3H), 2.9 (s, 3H), 3.55 (t, 2H), 4.13 (t, 2H), 4.25 (m, 1H), 5.37 (m, 1H), 6.4 (d, 2H), 7.33 (d, 2H), 7.58 (d, 1H), 7.75 (d, 1H), 8.5 (d, 1H), 9.22 (s, 1H); m/z 460.

Workup

  1. filtrationThe reaction was filtered
  2. washthe filtered solid washed with DCM
  3. additionmore DCM added
  4. washThe solution was washed in turn with water (twice), saturated sodium chloride
  5. dry with materialdried with anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe product so obtained
  9. customboth were triturated with ether
  10. filtrationfiltered
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-22248485717543cca7c4836e313e3e15
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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