Acetic Anhydride → HCID 44578692, compound

HRID 1441329Notes

Reaction equation

HRID 1441329 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.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl.CO>[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][C:36](=[O:38])[CH3:37])[CH2:5]3)=[CH:11][CH:10]=2)=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68686065HCID 68686065, compound

Product 1

HCID 44578692HCID 44578692, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent2×

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), acetic anhydride (30 μl, 0.317 mM) was added. The reaction was stirred at room temperature under nitrogen for 2.5 hours. A few drops of MeOH were added and the solution stirred for 10 minutes. The reaction mixture was then diluted with more DCM and the solution extracted in turn with water (twice) and saturated sodium chloride. The organic layer was then dried with anhydrous sodium sulphate, filtered and evaporated. The crude product was triturated with ether, filtered washed with ether and dried to give the title compound as a yellow solid (99 mg, 81%). NMR 1.4 (d, 6H), 1.8 (s, 3H), 2.5 (s, 3H+DMSO), 3.5 (t, 2H), 4.05 (t, 2H), 4.53 (m, 1H), 5.43 (m, 1H), 6.4 (d, 2H), 7.33 (m, 3H), 8.42 (m, 2H), 9.08 (s, 1H); m/z 424.

Workup

  1. stirringthe solution stirred for 10 minutes
  2. extractionthe solution extracted in turn with water (twice) and saturated sodium chloride
  3. dry with materialThe organic layer was then dried with anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was triturated with ether
  7. filtrationfiltered
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-69c9fddb86664613a547dd56d34bff0a
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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