Dimethylamine → HCID 71243530, compound

HRID 1774447Notes

Reaction equation

HRID 1774447 reaction equation
[OH:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.C[CH2:31][N:32](CC)[CH2:33]C.CNC.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl>[OH:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:32]([CH3:33])[CH3:31])=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 601550231380445-03-3

Product 1

HCID 71243530HCID 71243530, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(((1S,2S)-1-hydroxy-2,3-dihydro-1H,1′H-[2,2′-biinden]-2-yl)methyl)benzoic acid (100 mg, 0.26 mmol), Et3N (157 mg, 1.56 mmol) and dimethyl amine (0.33 mL, 2.0 M solution in THF, 0.65 mmol) in DCM (5 mL), was added T3P (0.33 mL, 50 wt % solution in ethyl acetate, 0.52 mmol) and then stirred at room temperature for 12 h. The reaction mixture was quenched with water (25 mL) and extracted with DCM (3×25 mL). The organic layer was washed with brine (25 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by CombiFlash using 20% ethyl acetate in chloroform as an eluent to yield 80 mg (75%) of the title compound as an off white solid.

Workup

  1. customThe reaction mixture was quenched with water (25 mL)
  2. extractionextracted with DCM (3×25 mL)
  3. washThe organic layer was washed with brine (25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-e66f95484a5446f6a035686297b1bf4a
Source dataset
uspto-grants-2016_02
Patent number
US09260376B2

Reaction notes

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