Dicyclohexylcarbodiimide → HCID 25255366, compound

HRID 507397Notes

Reaction equation

HRID 507397 reaction equation
[CH3:1][C:2]1[N:3]([CH2:20][C:21]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=2)=[O:22])[C:4](=[O:19])[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:32][CH:33]([CH3:37])[CH:34]([NH2:36])[CH3:35].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:35][CH:34]([NH:36][C:27](=[O:29])[C:26]1[CH:30]=[CH:31][C:23]([C:21](=[O:22])[CH2:20][N:3]2[C:4](=[O:19])[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:6]=[C:2]2[CH3:1])=[CH:24][CH:25]=1)[CH:33]([CH3:37])[CH3:32]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 117311,2-DimethylpropylamineHCID 68466882HCID 68466882, compound

Product 1

HCID 25255366HCID 25255366, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(2-Methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-acetyl]-benzoic acid (120 mg, 0.29 mmol) and (+/−)-3-methyl-2-butylamine (45 uL, 0.44 mmol) and N,N′-dicyclohexylcarbodiimide (97 mg, 0.47 mmol) and 4-(dimethylamino)-pryridine (58 mg, 0.47 mmol) are dissolved in 5 mL methylene chloride. The reaction mixture is stirred for 12 hours, filtrated and the filtrate evaporated. The residue of the filtrate is purified by preparative HPLC (Method 1) to yield (+/−)-N-(1,2-dimethyl-propyl)-4-[2-(2-methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-acetyl]-benzamide (68 mg, 48%). LCIMS at 354 nm; [M+H] 482; Rt 3.304 min.

Workup

  1. filtrationfiltrated
  2. customthe filtrate evaporated
  3. customThe residue of the filtrate is purified by preparative HPLC (Method 1)

Sources & evidence

ORD record
ord-55be12460e484082a160b801a4ab4e51
Source dataset
uspto-grants-2010_08
Patent number
US07786155B2

Reaction notes

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