Dimethylamine → HCID 69130208, compound

HRID 2253280Notes

Reaction equation

HRID 2253280 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:18][CH:17]=2)[C:13](O)=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:47]([CH3:49])[CH3:48])C2C=CC=CC=2N=N1.CNC.C1COCC1>CN(C=O)C.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:20][CH:21]=2)[C:13]([N:47]([CH3:49])[CH3:48])=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69130673HCID 69130673, compound

Product 1

HCID 69130208HCID 69130208, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 3-(3,5-dimethoxyphenyl)-2-[4-(pyridin-2-yloxy)-phenyl]-acrylic acid, 65, (0.11 g, 0.3 mmol), benzotriazol-1-yloxytris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, 0.15 g, 0.35 mmol), dimethylamine in THF (2M, 0.5 mL, 1.0 mmol), triethylamine ( 0.035 g, 035 mmol) in DMF (6.0 mL) was stirred for 3 h at room temperature. The reaction mixture was poured in water (50.0 mL) and extracted with ethyl acetate (2×50 mL). Solvent was evaporated under reduced pressure and residue was purified by silica gel chromatography to yield 66.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. customSolvent was evaporated under reduced pressure and residue
  3. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-b4dc430b093048b5b528d7fa7352f6f9
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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