1,1'-Carbonyldiimidazole → HCID 17751089, compound

HRID 2427477Notes

Reaction equation

HRID 2427477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][CH:22]=2)[CH:5]=[C:6]([Cl:20])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]1=[O:19].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[F:43][C:44]([F:52])([F:51])[CH:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([N:48]3[CH2:49][CH2:50][CH:45]([C:44]([F:52])([F:51])[F:43])[CH2:46][CH2:47]3)=[O:28])=[CH:25][CH:26]=2)[CH:5]=[C:6]([Cl:20])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][C:11]2([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:10]1=[O:19]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 24863749HCID 24863749, compound

Product 1

HCID 17751089HCID 17751089, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of Example 4 (0.079 g, 0.18 mmol) in CH2Cl2 (8 mL) with 1,1′-carbonyldiimidazole (0.047 g, 0.29 mmol) and stir for 1 hour at room temperature under N2. Then, treat the reaction with 4-(trifluoromethyl)piperidine HCl (0.087 g, 0.46 mmol) and diisopropylethylamine (0.12 g, 0.92 mmol) and stir for 16 hours at room temperature under N2. Dilute the reaction with ethyl acetate and wash with 1N HCl and water. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify on silica with a 0 to 10% methanol in CH2Cl2 gradient on silica gel and then isocratically with 50/50 ethyl acetate/hexanes gradient on silica gel to afford 0.067 g (64%) of the titled product. Rf=0.68 (9/1 CH2Cl2/methanol). MS (m/z): 567 (M+).

Workup

  1. additionThen, treat
  2. stirringstir for 16 hours at room temperature under N2
  3. additionDilute
  4. washwash with 1N HCl and water
  5. dry with materialDry the organic layer with Na2SO4
  6. customremove the solvent in vacuo
  7. customto afford crude product
  8. customPurify on silica with a 0 to 10% methanol in CH2Cl2 gradient on silica gel

Sources & evidence

ORD record
ord-ce465833f0b243868b6c43a62ec4a20b
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Reaction notes

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