Dichloromethane → HCID 59397874, compound

HRID 2193230Notes

Reaction equation

HRID 2193230 reaction equation
ClCCl.[C:4]([O:8][C:9]([N:11]([CH2:35][C:36]1[CH:45]=[CH:44]C2OCCOC=2[CH:37]=1)[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30](O)=[O:31])[CH:28]=3)[C:23]([CH3:33])=[CH:22][C:21]2=[O:34])[CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl.[CH3:47][NH:48][CH3:49].F[P-](F)(F)(F)(F)F.N1([O:66][C:67](N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:74]([O:77][CH2:78]C)(=O)[CH3:75]>O.C(N(CC)CC)C>[O:66]1[C:67]2[CH:44]=[CH:45][C:36]([CH2:35][N:11]([CH:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][N:20]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:30]([N:48]([CH3:49])[CH3:47])=[O:31])[CH:28]=5)[C:23]([CH3:33])=[CH:22][C:21]4=[O:34])[CH2:16][CH2:17]3)[C:9](=[O:10])[O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:37][C:78]=2[O:77][CH2:74][CH2:75]1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59397939HCID 59397939, compound

Product 1

HCID 59397874HCID 59397874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 1.7 mL of a dichloromethane solution containing 0.10 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-4-methyl-2-oxo-1,2-dihydroquinoline-7-carboxylic acid, 89 μL of triethylamine, 51 mg of dimethylamine hydrochloride and 0.12 g of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate were added at room temperature, and stirred at the same temperature for 1 hour. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography [eluent; chloroform:methanol=100:1], to give 93 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-((dimethylamino)carbonyl)-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white solid.

Workup

  1. additionwere added at room temperature
  2. customThe organic layer was separated
  3. washwashed with aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by basic silica gel column chromatography [eluent; chloroform:methanol=100:1]

Sources & evidence

ORD record
ord-55b7cd95f1fc4b9c9d7922ca85d89e78
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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