Dimethylamine → HCID 69154619, compound

HRID 2253282Notes

Reaction equation

HRID 2253282 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[C:12](=[O:16])C(O)=O)=[CH:9][C:4]=2[O:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:55]([CH3:57])[CH3:56])C2C=CC=CC=2N=N1.C(N(CC)CC)C.CNC.C1COCC1>CN(C=O)C.O>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C:20]2[CH:21]=[CH:22][C:17]([C:11]([C:12](=[O:16])[N:55]([CH3:57])[CH3:56])=[CH:10][C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)=[CH:18][CH:19]=2)=[CH:25][CH:26]=1)[CH3:36]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69155893HCID 69155893, compound

Product 1

HCID 69154619HCID 69154619, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-benzo[1,3]dioxol-5-yl-3-{4-[4-(2-ethoxycarbonylethyl)-phenoxy]-phenyl}-2-oxobut-3-enoic acid, 68, (0.08 g, 0.17 mmol), benzotriazol-1-yloxytris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, 0.09 g, 0.21 mmol), triethylamine (36 μL, 0.25 mmol), dimethylamine in THF (2M, 0.25 mL, 0.5 mmol) in DMF (2.0 mL) was stirred for 10 min at room temperature. Reaction mixture was poured in water (20 mL). Solid separated was filtered and boiled in toluene, cooled and filtered. Crude solid was purified by silica gel chromatography to yield 69.

Workup

  1. customReaction mixture
  2. customSolid separated
  3. filtrationwas filtered
  4. temperaturecooled
  5. filtrationfiltered
  6. customCrude solid was purified by silica gel chromatography

Sources & evidence

ORD record
ord-309fcb917b354f878b709490c78a4bd6
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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