Dicyclohexylcarbodiimide → HCID 58189254, compound

HRID 1423150Notes

Reaction equation

HRID 1423150 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](=[O:37])[C:34](O)=[O:35].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:34](=[O:35])[C:33]([C:29]1[S:28][CH:32]=[CH:31][CH:30]=1)=[O:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 776942-Thiopheneglyoxylic acidHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Product 1

HCID 58189254HCID 58189254, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (74 mg, 0.20 mmol) in CH2Cl2 (1 mL) at 0-5° C. was treated with a catalytic amount of 4-dimethylaminopyridine (DMAP) and 2-thiophene glyoxylic acid (37 mg, 0.24 mmol) followed by DCC (50 mg, 0.24 mmol). The reaction mixture was allowed to warm to room temperature and stir for 3 h. After this time the reaction mixture was evaporated and the residue purified by silica gel flash chromatography with 25% then 35% EtOAc/hexanes as eluant to afford the title compound as yellow foam (93 mg, 93%). LC/MS (Method B) 4.27 min, [M+1]+ 505.

Workup

  1. customAfter this time the reaction mixture was evaporated
  2. customthe residue purified by silica gel flash chromatography with 25%

Sources & evidence

ORD record
ord-eb1cc96f2f40427dbcf9ca31cd00b5b6
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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