Dichloromethane → tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methyl-7-((methylamino) carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 2193202Notes

Reaction equation

HRID 2193202 reaction equation
ClCCl.[C:4]([O:8][C:9]([N:11]([CH2:35][C:36]1[CH:45]=[CH:44][C:39]2[O:40][CH2:41][CH2:42][O:43][C:38]=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]([OH:32])=O)[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.CN.F[P-](F)(F)(F)(F)F.[N:56]1(OC(N(C)C)=[N+](C)C)[C:60]2N=CC=CC=2N=N1>C(OCC)(=O)C.O.C(N(CC)CC)C>[C:4]([O:8][C:9](=[O:10])[N:11]([CH2:35][C:36]1[CH:45]=[CH:44][C:39]2[O:40][CH2:41][CH2:42][O:43][C:38]=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]([NH:56][CH3:60])=[O:32])[CH:28]=3)[C:23]([CH3:33])=[CH:22][C:21]2=[O:34])[CH2:14][CH2:13]1)([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 6364545Methylamine hydrochloride2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 59397939HCID 59397939, compound

Product 1

HCID 59398071tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methyl-7-((methylamino) carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamateYield 56.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 1.7 mL of 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, 13 mg of methylamine hydrochloride, 0.12 g of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate and 89 μL of triethylamine were added at room temperature, stirred for 30 min, and allowed to stand for 12 hours. Further, 13 mg of methylamine hydrochloride, 0.12 g of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, and 89 μL of triethylamine were added. Water and ethyl acetate were added, the insoluble material was filtered off, 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:water=100:1], to give 58 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methyl-7-((methylamino)carbonyl)-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)carbamate as a brown oil.

Workup

  1. additionwere added at room temperature
  2. waitto stand for 12 hours
  3. filtrationthe insoluble material was filtered off
  4. customthe organic layer was separated
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by basic silica gel column chromatography [eluent; chloroform:water=100:1]

Sources & evidence

ORD record
ord-1dc74e82b8f749ab926f9546e5dac051
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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