Triethylamine → HCID 87568165, compound

HRID 1171723Notes

Reaction equation

HRID 1171723 reaction equation
FC(F)(F)C(O)=O.[C:8]([S:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14]/[C:13]/1=[CH:18]\[C:19]1[N:20]=[C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[S:22][CH:23]=1)(=[O:10])[CH3:9].Br[CH:33]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[F:45])[C:34]([CH:36]1[CH2:38][CH2:37]1)=[O:35].C(N(CC)CC)C>C(#N)C>[C:8]([S:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:33]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])[C:34]([CH:36]2[CH2:37][CH2:38]2)=[O:35])[CH2:14]/[C:13]/1=[CH:18]\[C:19]1[N:20]=[C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[S:22][CH:23]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-oneHCID 87565600HCID 87565600, compound

Product 1

HCID 87568165HCID 87568165, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following a procedure similar to that described in Example 132-(g), (E)-4-(acetylsulfanyl)-3-{[2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}piperidine hydrogen trifluoroacetate (420 mg) was subjected to the reaction with 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone (340 mg) and triethylamine (310 μl) in acetonitrile (5 ml). The product obtained by usual extraction was purified by silica gel chromatography (eluent: hexane/ethylacetate=2/1˜2/3) to afford (E)-4-(acetylsulfanyl)-3-{[2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine (230 mg) as a pale yellow amorphous solid.

Workup

  1. customThe product obtained by usual extraction
  2. customwas purified by silica gel chromatography (eluent: hexane/ethylacetate=2/1˜2/3)

Sources & evidence

ORD record
ord-4d62e791621f406cabc751544f4d552f
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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