Diisopropylethylamine → 4-Guanidinomethyl-benzoic acid methyl ester dihydrate

HRID 416225

反応式

HRID 416225 の反応式
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.Cl.[N:15]1([C:20](N)=[NH:21])C=CC=N1.CCN(C(C)C)C(C)C>C(O)C>[OH2:9].[OH2:9].[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][NH:2][C:20]([NH2:21])=[NH:15])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 2734672Pyrazole-1-carboxamidine monohydrochloride

生成物 1

HCID 1784979354-Guanidinomethyl-benzoic acid methyl ester dihydrate収率 233.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of methyl 4-(aminomethyl)benzoate hydrochloride (5 g) in dry ethanol (25 mL) was added 1H-pyrazole-1-carboxamidine hydrochloride (4.4 g) followed by DIPEA (13.0 mL) and the mixture was refluxed for 3 h. Ethanol was removed under vacuum. To the remaining viscous oil saturated solution of NaHCO3 (50 mL) was slowly added under vigorous stirring followed by addition of 300 ml water (resultant pH 9). A white solid is formed and stirring was continued for 1 h. This material was filtered off, washed with water (200 mL) and tert-butyl methyl ether (50 mL), and dried to give the title compound 24 as a white powder (4.7 g, 91%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.91 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.0 Hz, 2H), 4.39 (s, 2H), 3.83 (s, 3H), 3.80-2.80 [m, 4H+2H2O (determined by elemental analysis]).

後処理

  1. temperaturethe mixture was refluxed for 3 h
  2. customEthanol was removed under vacuum
  3. additionTo the remaining viscous oil saturated solution of NaHCO3 (50 mL) was slowly added
  4. additionfollowed by addition of 300 ml water (resultant pH 9)
  5. customA white solid is formed
  6. stirringstirring
  7. filtrationThis material was filtered off
  8. washwashed with water (200 mL) and tert-butyl methyl ether (50 mL)
  9. customdried

出典と根拠

ORDレコード
ord-ef3faf379faf464c9611f50c51e31be0
出典データセット
uspto-grants-2012_01
特許番号
US08088805B2

関連ノート

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