Diisopropylethylamine → 4-(Methoxymethyl)-4'-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl

HRID 1519670ノート

反応式

HRID 1519670 の反応式
Cl.[CH3:2][NH:3][C:4](=[O:12])[C@H:5]([C:8](=[O:11])[O:9][CH3:10])[NH:6][CH3:7].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]2[CH:60]=[CH:59][C:58]([C:61]([OH:63])=O)=[CH:57][CH:56]=2)=[CH:51][CH:50]=1>[Cl-].[Na+].O.CN(C=O)C>[CH3:46][O:47][CH2:48][C:49]1[CH:50]=[CH:51][C:52]([C:55]2[CH:56]=[CH:57][C:58]([C:61](=[O:63])[N:6]([CH:5]([C:4]([NH:3][CH3:2])=[O:12])[C:8]([O:9][CH3:10])=[O:11])[CH3:7])=[CH:59][CH:60]=2)=[CH:53][CH:54]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712682094'-(Methoxymethyl)biphenyl-4-carboxylic acidHCID 86679246N,N2,O-trimethyl-3-oxoserinamide hydrochloride

生成物 1

HCID 712681484-(Methoxymethyl)-4'-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl収率 70%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

Intermediate 5-2 (0.39 g), HATU (0.57 g) and DIPEA (0.80 mL) were added to a DMF (6.0 mL) solution of 4′-(methoxymethyl)biphenyl-4-carboxylic acid (0.36 g) as obtained in Example 3-(3), and the mixture was stirred for 30 minutes at 80° C. Then, brine was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered out, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→0/100) to obtain 4-(methoxymethyl)-4′-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (yellow oil) (0.40 g, 69%).

後処理

  1. customas obtained in Example 3-(3)
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered out
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→0/100)

出典と根拠

ORDレコード
ord-c3caa28f1c3a4b93a75f9ba6fdb9196d
出典データセット
uspto-grants-2015_07
特許番号
US09073821B2

反応ノート

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