Triethylamine → HCID 59263845, compound

HRID 644972Notes

Reaction equation

HRID 644972 reaction equation
[C:1]([N:5]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH2:6][CH2:7][N:8]([CH2:19][CH2:20][C:21]1[C:29]2[S:28][C:27](=[O:30])[NH:26][C:25]=2[C:24]([OH:31])=[CH:23][CH:22]=1)[C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.Cl.[F:46][C:47]1[CH:48]=[C:49]([CH:53]=[C:54]([F:56])[CH:55]=1)[CH2:50][CH2:51][NH2:52]>C(O)C>[CH:32]1([N:5]([C:1](=[O:4])[CH2:2][CH2:3][NH:52][CH2:51][CH2:50][C:49]2[CH:53]=[C:54]([F:56])[CH:55]=[C:47]([F:46])[CH:48]=2)[CH2:6][CH2:7][N:8]([CH2:19][CH2:20][C:21]2[C:29]3[S:28][C:27](=[O:30])[NH:26][C:25]=3[C:24]([OH:31])=[CH:23][CH:22]=2)[C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59263885HCID 59263885, compoundHCID 66523759HCID 66523759, compound

Product 1

HCID 59263845HCID 59263845, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl {2-[acryloyl(cyclohexyl)amino]ethyl}[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]carbamate prepared as in Example 12 step i) (0.33 g), triethylamine (0.176 mL) and 3,5-difluorophenethylamine hydrochloride (0.244 g) were stirred in ethanol (3 mL) at 60° C. for 44 h. The mixture was cooled to room temperature, quenched with water (30 mL), extracted with ethyl acetate (50 mL), the organic extracts washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by flash silica chromatography with 10% methanol/dichloromethane as eluent. The pure fractions were evaporated to dryness to afford the sub-title product (0.35 g) as a colourless gum.

Workup

  1. customquenched with water (30 mL)
  2. extractionextracted with ethyl acetate (50 mL)
  3. washthe organic extracts washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by flash silica chromatography with 10% methanol/dichloromethane as eluent
  8. customThe pure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-5ef0061530184e099e72a7375d0c2717
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

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