Triethylamine → HCID 59331377, compound

HRID 1881970Notes

Reaction equation

HRID 1881970 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][C@H:19]3[CH2:39][CH2:38][C:21]4([O:25][C@H:24]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C@@H:23]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[O:22]4)[CH2:20]3)[C:14](=O)[CH:15]=[CH2:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[N:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH:46]=O.C([N:50](CC)CC)C.C([O-])(=O)C.[NH4+]>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(O)(=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]3[NH:50][C:46]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][N:40]=4)=[CH:16][CH:15]=3)[CH2:18][C@H:19]3[CH2:39][CH2:38][C:21]4([O:22][C@H:23]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[C@@H:24]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)[O:25]4)[CH2:20]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 142732-PyridinecarboxaldehydeHCID 517165Ammonium AcetateHCID 59331254HCID 59331254, compound

Product 1

HCID 59331377HCID 59331377, compoundYield 12%

Reagents, catalysts & solvents 4

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-[4-(cyclopropylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-one (500 mg) in ethanol (5 mL) were added pyridine-2-carbaldehyde (107 μL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (28 mg) and triethylamine (56 μL), and the mixture was stirred with heating under reflux for 2 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a crude product (610 mg). To a solution of the obtained crude product (610 mg) in acetic acid (5 mL) was added ammonium acetate (1135 mg), and the mixture was stirred at 110° C. for 45 min. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative HPLC to give the title compound (70 mg, yield 12%) as a colorless amorphous solid. MS: 631 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give a crude product (610 mg)
  8. stirringthe mixture was stirred at 110° C. for 45 min
  9. temperatureAfter cooling to room temperature
  10. washwashed with water
  11. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-4d923a43c4694252b9d0ba0c819d6f49
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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