Diisopropylethylamine → 4-Guanidinomethyl-benzoic acid methyl ester dihydrate

HRID 416225

반응식

HRID 416225 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 1784979354-Guanidinomethyl-benzoic acid methyl ester dihydrate수율 233.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]).

후처리

  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

출처 및 근거

ORD 기록
ord-ef3faf379faf464c9611f50c51e31be0
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088805B2

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