1,1'-Carbonyldiimidazole → HCID 57672047, compound

HRID 1692096Notes

Reaction equation

HRID 1692096 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([OH:37])=O)=[CH:31][CH:30]=2)[CH:12]=[C:13]([Cl:28])[C:14]=1[CH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:17]1=[O:27].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[F:51][C:52]([F:60])([F:59])[CH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[C:11]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([N:56]3[CH2:57][CH2:58][CH:53]([C:52]([F:60])([F:59])[F:51])[CH2:54][CH2:55]3)=[O:37])=[CH:33][CH:34]=2)[CH:12]=[C:13]([Cl:28])[C:14]=1[CH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:17]1=[O:27]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 66905271HCID 66905271, compound

Product 1

HCID 57672047HCID 57672047, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Treat a mixture of (R)-3′,5′-dichloro-4′-(1-morpholin-4-yl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carboxylic acid trifluoro acetate (0.16 g, 0.28 mmol) in CH2Cl2 (10 mL) with 1,1′-carbonyldiimidazole (0.092 g, 0.57 mmol), 4-trifluoromethylpiperidine hydrochloride (0.081 g, 0.43 mmol) and diisopropylethylamine (0.110 g, 0.86 mmol) and stir for 12 hours at room temperature. Load the mixture on silica gel column and flash with 50% ethyl acetate in hexanes to 100% ethyl acetate to afford 0.081 g of a mixture of the title compound and impurity. Re-purify via reverse phase HPLC to afford 0.055 g (34%) of the title compound. MS (m/z): 584 (M+).

Workup

  1. additionTreat

Sources & evidence

ORD record
ord-560f94021f334805ae41ca624df6035a
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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