Difluoroacetic acid → HCID 178498370、化合物

HRID 44548

反応式

HRID 44548 の反応式
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:19][CH:20]([F:24])[C:21](O)=O>C1(C)C=CC=CC=1>[F:19][CH:20]([F:24])[C:21]1[NH:1][C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][C:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:10][C:11]=2[N:12]=1

参加物

4

反応物 2

HCID 9788Difluoroacetic acidHCID 58279190Methyl 2,3-diamino-5-morpholinobenzoate

生成物 1

HCID 178498370HCID 178498370、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of methyl 2,3-diamino-5-morpholinobenzoate (40.16 g, 160 mmol) and 2,2-difluoroacetic acid (46.08 g, 480 mmol) in toluene (500 mL) was stirred at reflux temperature for 15 h. Then the mixture was cooled to room temperature and the solvent was removed in vacuum. The residue was purified by silica gel chromatography eluted with petroleum ether:EtOAc=2:1 to afford the desired product. Then, it was dissolved with EtOAc (2 L) and washed with aqueous NaHCO3 (1 L) and brine (1 L). The organic layer was dried over anhydrous Na2SO4 and concentrated to give the desired product (40.9 g, 82%) as a yellow solid. 1H NMR showed this compound is in a form of tautomeric mixture (major tautomer/minor tautomer=5/1) 1H NMR of the major tautomer (300 MHz, DMSO-d6): δ ppm 3.14 (t, 4H, J=4.8 Hz), 3.78 (t, 4H, J=4.8 Hz), 3.96 (s, 3H), 7.21 (t, 1H, J=52.8 Hz), 7.55 (d, 1H, J=2.4 Hz), 7.65 (d, 1H, J=2.4 Hz), 12.92 (s, 1H); LC-MS: m/e=312 [M+1]+

後処理

  1. temperatureat reflux temperature for 15 h
  2. customthe solvent was removed in vacuum
  3. customThe residue was purified by silica gel chromatography
  4. washeluted with petroleum ether

出典と根拠

ORDレコード
ord-bb4f66d5fc0e4c1bb4198b86bbfc5930
出典データセット
uspto-grants-2013_09
特許番号
US08541411B2

関連ノート

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