2-Ethylbutyric acid → 2-ethyl-N-{4-[2-(2-methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-ethyl]-phenyl}-butyramide

HRID 507400Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=[C:11]2[CH3:28])=[CH:4][CH:3]=1.[CH2:29]([CH:31]([CH2:35][CH3:36])[C:32](O)=[O:33])[CH3:30].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(C(C)C)C(C)C)C>C(Cl)Cl.O>[CH2:29]([CH:31]([CH2:35][CH3:36])[C:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:12]=[C:11]2[CH3:28])=[CH:6][CH:7]=1)=[O:33])[CH3:30]

Participants

Conditions

Temperature: 50 °C

Procedure

3-[2-(4-Amino-phenyl)-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one (56 mg, 0.15 mmol) is dissolved in 10 mL methylene chloride and 2-ethyl-butyric acid (18 mg, 0.15 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (113 mg, 0.24 mmol) and ethyl diisopropyl amine (42 uL, 0.24 mmol) are added. The mixture is stirred and heated to 50° C. for 5 hours. Subsequently water and methylene chloride are added the organic phase is separated, dried and evaporated. The residue is purified by preparative HPLC (Method 1) to yield 2-ethyl-N-{4-[2-(2-methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-ethyl]-phenyl}-butyramide (25 mg, 35%). LC/MS at 254 nm; [M+H] 468; Rt 3.351.

Workup

customis separated
customdried
customevaporated
customThe residue is purified by preparative HPLC (Method 1)

Sources & evidence

ORD record: ord-709ed9e2e3aa42eca8d1d7a6c62ef17a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786155B2

Reaction notes

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