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 2193202ノート

反応式

HRID 2193202 の反応式
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]

参加物

8

反応物 4

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

生成物 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)carbamate収率 56.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8471Triethylamine溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-1dc74e82b8f749ab926f9546e5dac051
出典データセット
uspto-grants-2012_12
特許番号
US08329694B2

反応ノート

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