Ammonium Chloride → 4-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,N-dimethyl-N-pent-4-enyl-benzamide

HRID 1755102Notes

Reaction equation

HRID 1755102 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:34][NH:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40].[CH2:41]([O:45][C:46]1[CH:47]=[C:48]([C:56]2[NH:60][C:59](=[O:61])[C:58]3([CH2:66][CH2:65][N:64]([S:67]([CH2:70][CH2:71][C:72]4[CH:80]=[CH:79][C:75]([C:76](O)=[O:77])=[CH:74][C:73]=4[CH3:81])(=[O:69])=[O:68])[CH2:63][CH2:62]3)[N:57]=2)[CH:49]=[C:50]([C:52]([F:55])([F:54])[F:53])[CH:51]=1)[CH2:42][CH:43]=[CH2:44].[Cl-].[NH4+]>CN(C=O)C>[CH2:41]([O:45][C:46]1[CH:47]=[C:48]([C:56]2[NH:60][C:59](=[O:61])[C:58]3([CH2:66][CH2:65][N:64]([S:67]([CH2:70][CH2:71][C:72]4[CH:80]=[CH:79][C:75]([C:76]([N:35]([CH3:34])[CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])=[O:77])=[CH:74][C:73]=4[CH3:81])(=[O:68])=[O:69])[CH2:63][CH2:62]3)[N:57]=2)[CH:49]=[C:50]([C:52]([F:53])([F:55])[F:54])[CH:51]=1)[CH2:42][CH:43]=[CH2:44]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 541660N-methylpent-4-en-1-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668170254-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid

Product 1

HCID 668173174-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,N-dimethyl-N-pent-4-enyl-benzamideYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (194 mg, 0.510 mmol), N,N-diisopropylethylamine (143 μL) and methyl-pent-4-enyl-amine (80 mg) were added to a solution of 4-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid (200 mg, 0.337 mmol) in DMF (3 ml), and the mixture was stirred at room temperature overnight. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,N-dimethyl-N-pent-4-enyl-benzamide (192 mg, 84%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-45398500cf5f4070a553214abcffc66e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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