1,1'-Carbonyldiimidazole → HCID 67354701, compound

HRID 1670822Notes

Reaction equation

HRID 1670822 reaction equation
[C:1]([Si:5]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([OH:34])=O)=[CH:28][CH:27]=4)=[CH:21][C:20]=3[Cl:35])[C:14]2=[O:36])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[F:62][C:63]([F:71])([F:70])[CH:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)(=O)C>[C:1]([Si:5]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:6][CH:7]1[CH2:8][CH2:9][CH:10]([CH:13]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[C:20]([Cl:35])=[CH:21][C:22]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([N:67]5[CH2:68][CH2:69][CH:64]([C:63]([F:71])([F:70])[F:62])[CH2:65][CH2:66]5)=[O:34])=[CH:28][CH:27]=4)=[CH:23][C:24]=3[Cl:25])[C:14]2=[O:36])[CH2:11][CH2:12]1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 67355400HCID 67355400, compound

Product 1

HCID 67354701HCID 67354701, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 4′-{3-[4-(tert-Butyl-diphenyl-silanyloxy)-cyclohexyl]-2-oxo-pyrrolidin-1-ylmethyl}-3′,5′-dichloro-biphenyl-4-carboxylic acid (0.35 g, 0.5 mmol) in CH2Cl2 (20 mL) with 1,1′-carbonyldiimidazole (0.162 g, 1.0 mmol) and stir for 45 minutes at room temperature. Treat the reaction with 4-trifluoromethylpiperidine hydrochloride (0.142 g, 0.75 mmol) and diisopropylethylamine (0.097 g, 0.75 mmol), and stir for 12 hours at room temperature. Load the mixture on silica gel column and flash with 25% to 50% ethyl acetate in hexanes to afford 0.21 g (50%) of the title compound. MS (m/z): 835 (M+).

Workup

  1. additionTreat
  2. stirringstir for 12 hours at room temperature

Sources & evidence

ORD record
ord-5477ff449d4844c7be26818f3d41ab3a
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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