Tetrahydrofuran → HCID 178525208, compound

HRID 1601887Notes

Reaction equation

HRID 1601887 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10](=[O:62])[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]2[C:45]3[C:40](=[C:41]4[CH:53]=[CH:52][CH:51]=[CH:50][C:42]4=[C:43]4[CH:49]=[CH:48][CH:47]=[CH:46][C:44]4=3)[C:39]3[C:34]2=[C:35]2[CH:61]=[CH:60][CH:59]=[CH:58][C:36]2=[C:37]2[CH:57]=[CH:56][CH:55]=[CH:54][C:38]2=3)=[CH:18][CH:17]=1)=[O:13].[CH:63]1([NH2:66])[CH2:65][CH2:64]1.[CH2:67]1COCC1>>[CH:63]1([NH:66][CH:67]=[C:11]([C:10](=[O:62])[C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[F:1])[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]3[C:45]4[C:40](=[C:41]5[CH:53]=[CH:52][CH:51]=[CH:50][C:42]5=[C:43]5[CH:49]=[CH:48][CH:47]=[CH:46][C:44]5=4)[C:39]4[C:34]3=[C:35]3[CH:61]=[CH:60][CH:59]=[CH:58][C:36]3=[C:37]3[CH:57]=[CH:56][CH:55]=[CH:54][C:38]3=4)=[CH:18][CH:17]=2)=[O:13])[CH2:65][CH2:64]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 69828CyclopropylamineHCID 9940747HCID 9940747, compound

Product 1

HCID 178525208HCID 178525208, compoundYield 34%

Procedure

To an oven-dried flask was added 4-[[10-(17H-tetrabenzo[a,c,g,i]fluoren-17-yl)-decyl]oxy]phenyl]-methyl 2,4,5-trifluoro-β-oxobenzenepropanoate (6) (122.5 mg, 0.148 mmol) and dissolved in freshly distilled THF (10 mL). The flask was purged with nitrogen and N,N-dimethylformamide diethyl acetal was added as a solution in THF (1 mL) via syringe. Glassware was washed with THF (2 mL). The solution was stirred at room temperature under an atmosphere of nitrogen for 24 hours. Cyclopropylamine (120.2 mg, 0.818 mmol) was added as a solution in THF (1 mL) and the resultant solution stirred at room temperature under nitrogen for 72 hours. The solution was quenched by the addition of saturated ammonium chloride solution (20 mL) and organic products extracted faith DCM (2×20 mL), dried over MgSO4 and solvent removed in vacuo to yield a dark yellow oil. This was purified by flash column chromatography using DCM as eluent to yield [4-[[10-(17H-tetrabenzo[a,c,g,i]fluoren-17-yl)-decyl]oxy]phenyl]methyl α-[(cyclopropylamino)-methylene]-2,4,5-trifluoro-β-oxobenzenepropanoate as a pale yellow solid (45.1 mg, 0.051 mmol, 34%).

Workup

  1. customThe flask was purged with nitrogen and N,N-dimethylformamide diethyl acetal
  2. additionwas added as a solution in THF (1 mL) via syringe
  3. washGlassware was washed with THF (2 mL)
  4. customThe solution was quenched by the addition of saturated ammonium chloride solution (20 mL) and organic products
  5. extractionextracted faith DCM (2×20 mL)
  6. dry with materialdried over MgSO4 and solvent
  7. customremoved in vacuo
  8. customto yield a dark yellow oil
  9. customThis was purified by flash column chromatography

Sources & evidence

ORD record
ord-0dd57dfb982e47c0a61fd119e48e0e50
Source dataset
uspto-grants-1999_11
Patent number
US05977400

Reaction notes

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