Acetic Acid → 1-[1-[(3S)-3-(3,4-Dichlorophenyl)-4-(5-phenyltetrazol-1-yl)butyl]-piperidin-4-yl]tetrahydropyrimidin-2-one dihydrochloride

HRID 277313노트

반응식

HRID 277313 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:13][N:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:17][N:16]=[N:15]2)[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:25]1[CH2:30][CH2:29][CH:28]([N:31]2[CH2:36][CH2:35][CH2:34][NH:33][C:32]2=[O:37])[CH2:27][CH2:26]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.ClCCl.C(=O)(O)[O-].[Na+]>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:13][N:14]2[C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:17][N:16]=[N:15]2)[CH2:10][CH2:11][N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:36][CH2:35][CH2:34][NH:33][C:32]3=[O:37])[CH2:27][CH2:26]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 155726661-(Piperidin-4-yl)-1,3-diazinan-2-oneHCID 57095043(3S)-3-(3,4-dichlorophenyl)-4-(5-phenyltetrazol-1-yl)-butyraldehyde

생성물 1

HCID 213086331-[1-[(3S)-3-(3,4-Dichlorophenyl)-4-(5-phenyltetrazol-1-yl)butyl]-piperidin-4-yl]tetrahydropyrimidin-2-one dihydrochloride수율 185.8%

시약·촉매·용매 3

HCID 887Methanol용매3회HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

(3S)-3-(3,4-dichlorophenyl)-4-(5-phenyltetrazol-1-yl)-butyraldehyde (0.90 g) in methanol (6 mL) and dichloromethane (2 mL) was added to a solution of 1-(piperidin-4-yl)tetrahydropyrimidin-2-one (0.458 g) and acetic acid (0.14 mL) in methanol (5 mL). After 40 minutes, sodium cyanoborohydride (0.157 g) in methanol (5 mL) was added in a single portion. After being stirred for 2 hours, the reaction mixture was diluted with aqueous sodium bicarbonate, stirred for 30 minutes, and extracted with dichloromethane. The organic extracts were dried, evaporated, and chromatographed, with dichloromethane:methanol (gradient 98:2, 70:30) as eluent. The purified material was dissolved in dichloromethane, precipitated out as the hydrochloride salt with ethereal hydrogen chloride, evaporated, and placed under high vacuum overnight to give the title compound as a white solid (0.928 g); NMR (CD3OD): 7.61-7.47 (m,3), 7.30 (m,2), 7.21 (d,1, J=8.2), 7.03 (d,1, J=2.1), 6.75 (dd,1, J=2.1, 8.3), 4.94 (dd,1, J=4.8, 14.2), 4.74 (dd,1, J=9.4, 14.2), 4.34 (m,1), 3.58 (m,2), 3.25 (m,5), 3.15-2.98 (m,3), 2.76 (m,1), 2.33-2.11 (m,4), 1.90 (m,4); MS: m/z=528(M+1). Analysis for C26H31Cl2N7O.0.15 Et2O.2.50 HCl: Calculated: C, 50.65; H, 5.59; N, 15.54; Found: C, 50.58; H, 5.61; N, 15.27.

후처리

  1. stirringstirred for 30 minutes
  2. extractionextracted with dichloromethane
  3. customThe organic extracts were dried
  4. customevaporated
  5. customchromatographed, with dichloromethane
  6. dissolutionThe purified material was dissolved in dichloromethane
  7. customprecipitated out as the hydrochloride salt with ethereal hydrogen chloride
  8. customevaporated
  9. customplaced under high vacuum overnight

출처 및 근거

ORD 기록
ord-62ec95730b3141f48b9e73cf28bd7c3d
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355695B1

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