1,1'-Carbonyldiimidazole → HCID 66905040, compound

HRID 1692091Notes

Reaction equation

HRID 1692091 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([OH:40])=O)=[CH:34][CH:33]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]2)[C:10]1=[O:31].C(N1C=CN=C1)(N1C=CN=C1)=O.[ClH:53].[F:54][C:55]([F:63])([F:62])[CH:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:53][C:34]1[CH:33]=[C:32]([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][C@@H:9]3[CH2:13][CH2:12][N:11]([N:14]4[CH2:15][CH2:16][CH:17]([O:20][Si:21]([CH:22]([CH3:23])[CH3:24])([CH:25]([CH3:26])[CH3:27])[CH:28]([CH3:30])[CH3:29])[CH2:18][CH2:19]4)[C:10]3=[O:31])=[CH:2][CH:3]=2)[CH:37]=[CH:36][C:35]=1[C:38]([N:59]1[CH2:60][CH2:61][CH:56]([C:55]([F:63])([F:62])[F:54])[CH2:57][CH2:58]1)=[O:40]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 66904958HCID 66904958, compound

Product 1

HCID 66905040HCID 66905040, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 3′-chloro-4′-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid (0.2 g, 0.34 mmol) in CH2Cl2 (15 mL) with 1,1′-carbonyldiimidazole (0.11 g, 0.68 mmol) and stir for 60 minutes at room temperature. Treat the reaction with 4-trifluoromethylpiperidine hydrochloride (0.10 g, 0.51 mmol) and diisopropylethylamine (0.07 g, 0.51 mmol) and stir for 12 hours at room temperature. Load the mixture on silica gel column, flash with 0% to 50% ethyl acetate in hexanes to afford 0.12 g (49%) of the title compound. MS (m/z): 720 (M+).

Workup

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

Sources & evidence

ORD record
ord-cf26ec29dc7b47e5a1a0be0ecf3b25fb
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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