Triethylamine → 1-[(5-Chloro-1H-indol-2-yl)methyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 536100

반응식

HRID 536100 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11]=O)=[CH:5]2.[BH3-]C#N.[Na+].CCN(CC)CC.Cl.C(O[C:28]([C:30]1[NH:31][CH:32]=[CH:33][C:34]=1[NH2:35])=[O:29])C.C([N:44]=[C:45]=[S:46])(=O)C1C=CC=CC=1>CO.CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][N:35]1[C:34]3[CH:33]=[CH:32][NH:31][C:30]=3[C:28](=[O:29])[NH:44][C:45]1=[S:46])=[CH:5]2

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 68284Benzoyl isothiocyanateHCID 5003444Sodium cyanoborohydride2회HCID 122033185-Chloro-1H-indole-2-carbaldehydeHCID 164270913-Amino-2-ethoxycarbonylpyrrole hydrochloride

생성물 1

HCID 115300321-[(5-Chloro-1H-indol-2-yl)methyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one수율 30.2%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

5-Chloro-1H-indole-2-carbaldehyde (0.15 g, 0.76 mmol), NaCNBH3 (0.040 g, 0.63 mmol) and Et3N (0.088 mL, 0.63 mmol) was added to a stirred solution of 3-amino-1H-pyrrole-2-carboxylic acid ethyl ester hydrochloride (0.12 g, 0.63 mmol) in methanol (3 mL). The resulting mixture was stirred at r.t. overnight. The reaction mixture was heated to 50° C. Additional NaCNBH3 (0.5 equiv.) was added and the mixture was stirred at 50° C. for 3 h. A few drops of HOAc was added, and after 1 h the reaction mixture was cooled to r.t. and was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2 mL) and methanol (2 mL). Benzoyl isothiocyanate (0.093 mL, 0.69 mmol) was added and after stirring at r.t. for 1 h the mixture was concentrated in vacuo. The residue was dissolved in ammonia (7N in methanol, 3 mL) and heated at 80° C. for 2 h. The precipitated product was filtered and washed through with methanol and diethyl ether, followed by purification by preparative HPLC, obtaining 0.063 g (30%) of the title compound as a solid.

후처리

  1. temperatureThe reaction mixture was heated to 50° C
  2. stirringthe mixture was stirred at 50° C. for 3 h
  3. temperatureafter 1 h the reaction mixture was cooled to r.t.
  4. concentrationwas concentrated in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2 (2 mL)
  6. stirringafter stirring at r.t. for 1 h the mixture
  7. concentrationwas concentrated in vacuo
  8. dissolutionThe residue was dissolved in ammonia (7N in methanol, 3 mL)
  9. temperatureheated at 80° C. for 2 h
  10. filtrationThe precipitated product was filtered
  11. washwashed through with methanol and diethyl ether
  12. customfollowed by purification by preparative HPLC

출처 및 근거

ORD 기록
ord-ab0040aa21174d41b45f9285feb324e9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859568B2

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