Triethylamine → methyl 4-chloro-1-(3-hydroxypropyl)-2-[(6-methoxy-4-methylpyridin-3-yl)amino]-1H-benzimidazole-7-carboxylate

HRID 1628490노트

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HRID 1628490 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])[C:3]=1[NH:17][C:18](=S)[NH:19][C:20]1[CH:21]=[N:22][C:23]([O:27][CH3:28])=[CH:24][C:25]=1[CH3:26].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:3]2[N:17]=[C:18]([NH:19][C:20]3[CH:21]=[N:22][C:23]([O:27][CH3:28])=[CH:24][C:25]=3[CH3:26])[N:12]([CH2:13][CH2:14][CH2:15][OH:16])[C:4]=2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632883Methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-{[(6-methoxy-4-methylpyridin-3-yl)carbamothioyl]amino}benzoate

생성물 1

HCID 68762858methyl 4-chloro-1-(3-hydroxypropyl)-2-[(6-methoxy-4-methylpyridin-3-yl)amino]-1H-benzimidazole-7-carboxylate수율 100.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

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온도
50 °C

실험 절차

A mixture of the resulting thiourea (3.90 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.70 g, 8.89 mmol), and triethylamine (1.2 mL) in tetrahydrofuran (40 mL) was stirred at 50° C. for 2 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether to give the title compound as a colorless powder (2.20 g, 8.89 mmol, 57% in 2 steps).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-48e068ea430741479403ac7e317fd340
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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