Dimethylamine → HCID 19600084, 화합물

HRID 611393노트

반응식

HRID 611393 반응식
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[C:11]1([C:17]2([C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[S:22][CH2:21][CH2:20][CH2:19][S:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:32]([N:34]([CH2:37]C)[CH2:35]C)C.C(P(=O)(OCC)OCC)#N.CNC.C=O>CN(C)C=O.O>[CH3:32][N:34]([CH2:37][C:3]1[O:2][C:6]2[CH2:7][N:8]([C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:23]([C:17]4([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)[S:22][CH2:21][CH2:20][CH2:19][S:18]4)=[CH:24][CH:25]=3)[CH2:9][CH2:10][C:5]=2[CH:4]=1)[CH3:35]

참가 물질

9

반응물 6

HCID 674DimethylamineHCID 712FormaldehydeHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 19599883HCID 19599883, 화합물HCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

생성물 1

HCID 19600084HCID 19600084, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 0.319 g (2.000 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.696 g (2.2 mmol) of 4-(2-phenyl-1,3-dithian-2-yl)benzoic acid and 1.1 ml (8.0 mmol) of triethylamine in 30 ml of N,N-dimethylformamide, 0.489 g (3.0 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. Water was added, followed by 2 extractions with ethyl acetate. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was dissolved in 10 ml of acetic acid; 0.270 ml (3.00 mmol) of 50% aqueous dimethylamine and 0.245 ml (3.00 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate, and extracted with ethyl acetate 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1) to yield the desired product.

후처리

  1. temperaturecooling
  2. extractionfollowed by 2 extractions with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe resulting crude product was dissolved in 10 ml of acetic acid
  7. stirringby stirring at 100° C. for 30 minutes
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. extractionextracted with ethyl acetate 2 times
  10. washThe combined organic layer was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)

출처 및 근거

ORD 기록
ord-bcc1a33502384b93822fbfe76da2b374
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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