Triethylamine → HCID 86651766, compound

HRID 241248Notes

Reaction equation

HRID 241248 reaction equation
[C:1]([O:5][C:6](=[O:47])[CH2:7][N:8]([C:16]1[CH:21]=[CH:20][C:19](Br)=[C:18]([CH:23]([CH2:34][C:35]2[N:36]=[N:37][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:39][CH:40]=2)[NH:24][S:25]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:47])[CH2:7][N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:23]([CH2:34][C:35]2[N:36]=[N:37][C:38]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:39][CH:40]=2)[NH:24][S:25]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[N:17]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86651767HCID 86651767, compound

Product 1

HCID 86651766HCID 86651766, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl({5-bromo-6-[(6-phenylpyridazin-3-ylmethyl)-(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}tert-butoxycarbonylamino)acetate (239 mg, 0.329 mmol) obtained in Example 1-(a) in ethanol (3.3 ml) were added triethylamine (322 μl, 2.31 mmol) and 10% palladium-active carbon (55% hydrate) (48 mg), followed by stirring at room temperature for 6 hours under hydrogen atmosphere at 1 atm. After completion of the reaction, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:1→1:10 (V/V)) and then to reversed phase column chromatography (column; Megabond Elut™ C18 (manufactured by Varian, Inc.), eluent; acetonitrile:water=0:1→1:0 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (153 mg) as a white foam. (Yield: 72%)

Workup

  1. customAfter completion of the reaction, insolubles
  2. filtrationwere filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionto reversed phase column chromatography (column; Megabond Elut™ C18 (manufactured by Varian, Inc.), eluent; acetonitrile:water=0:1→1:0 (V/V)), and fractions containing the desired compound
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-94d6cdc87d19415cb254bb842d319821
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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