1,1'-Carbonyldiimidazole → HCID 24815133, compound

HRID 1686068Notes

Reaction equation

HRID 1686068 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[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.[OH:43][CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]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:27]=[CH:26][C:25]([C:28]([N:47]3[CH2:48][CH2:49][CH:44]([OH:43])[CH2:45][CH2:46]3)=[O:29])=[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]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 67265844HCID 67265844, compound

Product 1

HCID 24815133HCID 24815133, compoundYield 89%

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 (0.102 g, 0.228 mmol) in CH2Cl2 (10 mL) with 1,1′-carbonyldiimidazole (0.074 g, 0.457 mmol) and stir for 1 hour at room temperature. Treat the reaction with 4-hydroxypiperidine (0.065 g, 0.34 mmol) and diisopropylethylamine (0.044 g, 0.34 mmol) and stir for 12 hours at room temperature. Purify the mixture on silica gel column with 100% ethyl acetate and 10% methanol in dichloromethane to afford 0.107 g (89%) of the title compound. MS (m/z): 530 (M+).

Workup

  1. additionTreat
  2. stirringstir for 12 hours at room temperature
  3. customPurify the mixture on silica gel column with 100% ethyl acetate and 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-73b6ae4aa92f43eb9dfcda6040e62f8e
Source dataset
uspto-grants-2012_04
Patent number
US08148534B2

Reaction notes

Loading…