1,1'-Carbonyldiimidazole → HCID 17751080, compound

HRID 1686067Notes

Reaction equation

HRID 1686067 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([OH:30])=O)=[CH:24][CH:23]=2)[CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[F:44][C:45]([F:53])([F:52])[CH:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([N:49]3[CH2:50][CH2:51][CH:46]([C:45]([F:53])([F:52])[F:44])[CH2:47][CH2:48]3)=[O:30])=[CH:26][CH:27]=2)[CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[C:10]1=[O:20]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 67265844HCID 67265844, compound

Product 1

HCID 17751080HCID 17751080, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (R)-3′,5′-dichloro-4′-(2-oxo-1-piperidin-1-yl-pyrrolidin-3-ylmethyl)-biphenyl-4-carboxylic acid (0.090 g, 0.2 mmol) in CH2Cl2 (10 mL) with 1,1′-carbonyldiimidazole (0.065 g, 0.4 mmol) and stir for 1 hour at room temperature. Treat the reaction with 4-trifluoromethylpiperidine hydrochloride (0.057 g, 0.3 mmol) and diisopropylethylamine (0.039 g, 0.3 mmol) and stir for 12 hours at room temperature. Purify on silica gel column with 25% to 75% ethyl acetate in hexanes to afford 0.065 g (55%) of the title compound. MS (m/z): 582 (M+).

Workup

  1. additionTreat
  2. stirringstir for 12 hours at room temperature
  3. customPurify on silica gel column with 25% to 75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b956591723334b5ea1040dff71745c58
Source dataset
uspto-grants-2012_04
Patent number
US08148534B2

Reaction notes

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