Diisopropylethylamine → HCID 87285698, compound

HRID 574269Notes

Reaction equation

HRID 574269 reaction equation
[C:1]([O:5][C:6](=[O:45])[NH:7][C@H:8]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH:19]([CH2:23][OH:24])[CH2:18]2)=[C:13]([CH3:25])[N:12]([CH2:26][C:27]2[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:30]=[CH:29][C:28]=2[F:37])[C:11]1=[O:38])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Br[CH2:56][C:57]1[O:58][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:60][CH:61]=1>ClCCl>[C:1]([O:5][C:6](=[O:45])[NH:7][C@H:8]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:56][C:57]3[O:58][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:60][CH:61]=3)[CH:19]([CH2:23][OH:24])[CH2:18]2)=[C:13]([CH3:25])[N:12]([CH2:26][C:27]2[C:32]([C:33]([F:35])([F:36])[F:34])=[CH:31][CH:30]=[CH:29][C:28]=2[F:37])[C:11]1=[O:38])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 67143015HCID 67143015, compound

Product 1

HCID 87285698HCID 87285698, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(R)-2-[3-(2-fluoro-6-trifluoromethyl-benzyl)-5-(3-hydroxymethyl-piperazin-1-yl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (0.028 mmol) in dichloromethane (2 mL) were added N,N-diisopropylethylamine (10 μl, 0.056 mol) and 2-bromomethyl-5-trifluoromethyl-furan (7.6 mg, 0.034 mmol) in the order, followed by stirring at room temperature for 6 hrs. After concentration of the solution, the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 1/2/1) and dried in a vacuum to afford 17 mg of a white oil (yield 77%).

Workup

  1. customAfter concentration of the solution, the residue was purified
  2. customdried in a vacuum

Sources & evidence

ORD record
ord-3006d4bf5d5d45c1a8cc8b2df305e76a
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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