HCID 67132976, compound → HCID 25153107, compound

HRID 545434Notes

Reaction equation

HRID 545434 reaction equation
[CH:1]1([N:4]2[C:8]([C:9]([N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[O:10])=[C:7]([C:22]3[CH:23]=[N:24][C:25]([N:28](CC4C=CC=CC=4)CC4C=CC=CC=4)=[CH:26][CH:27]=3)[N:6]=[C:5]2[C:43]2[CH:48]=[CH:47][C:46]([O:49][C:50]([F:53])([F:52])[F:51])=[CH:45][CH:44]=2)[CH2:3][CH2:2]1>Br.C(O)(=O)C>[NH2:28][C:25]1[N:24]=[CH:23][C:22]([C:7]2[N:6]=[C:5]([C:43]3[CH:48]=[CH:47][C:46]([O:49][C:50]([F:53])([F:52])[F:51])=[CH:45][CH:44]=3)[N:4]([CH:1]3[CH2:2][CH2:3]3)[C:8]=2[C:9]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:15][CH2:16]2)=[O:10])=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 67132976HCID 67132976, compound2×

Product 1

HCID 25153107HCID 25153107, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Conditions

Temperature
100 °C

Procedure

0.2 g (0.2 mmol) of [3-cyclopropyl-5-(6-dibenzylamino-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (intermediate 11) was dissolved in 3 ml of HBr/acetic acid and the mixture heated to 100° C. for 24 h. The solvent was evaporated and the residue taken up in CH2Cl2, washed with saturated sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. Purification by flash column chromatography [CH2Cl2/MeOH 8:2] afforded 0.05 g (39%) of the title compound as a colorless amorphous solid. MS: 541.2 (MH+)

Workup

  1. customThe solvent was evaporated
  2. washwashed with saturated sodium hydrogen carbonate solution
  3. dry with materialdried with sodium sulphate
  4. concentrationconcentrated
  5. customPurification by flash column chromatography [CH2Cl2/MeOH 8:2]

Sources & evidence

ORD record
ord-7c750ea4bfb44e218c9562c9a6b0ab86
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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