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Diisopropylethylamine → HCID 178478954, 화합물

HRID 2223829
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HRID 2223829 반응식
C([N:20]1[CH:24]=[C:23]([CH2:25][NH2:26])[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.[Cl:36][C:37]1[N:42]=[C:41]([NH:43][C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)[N:40]=[C:39]([NH:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[N:38]=1.C(OC(=O)C)C.Cl>C(#N)C.C(O)(=O)C.C(OCC)(=O)C.O>[ClH:36].[F:50][C:47]1[CH:46]=[CH:45][C:44]([NH:43][C:41]2[N:42]=[C:37]([NH:26][CH2:25][C:23]3[N:22]=[CH:21][NH:20][CH:24]=3)[N:38]=[C:39]([NH:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:40]=2)=[CH:49][CH:48]=1
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참가 물질

9

반응물 4

HCID 81531DiisopropylethylamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 230331686-Chloro-N~2~-(4-fluorophenyl)-N~4~-phenyl-1,3,5-triazine-2,4-diamineHCID 23033177(1-Trityl-1H-imidazol-4-yl)methanamine

생성물 1

HCID 178478954HCID 178478954, 화합물

시약·촉매·용매 4

HCID 176
Acetic Acid
용매
HCID 962Water용매2회
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A 678 mg portion of [(1-trityl-1H-imidazol-4-yl)methyl]amine was dissolved in 10.0 ml of acetonitrile, and 0.52 ml of diisopropylethylamine and 316 mg of the 6-chloro-N-(4-fluorophenyl)-N′-phenyl-1,3,5-triazine-2,4-diamine synthesized in Reference Example 1 were added thereto and stirred at 80° C. for 3 days. After cooling down to room temperature, the reaction solution was mixed with water and extracted with ethyl acetate. The organic layer was washed with citric acid aqueous solution and saturated brine and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol (99:1) to obtain a crude product. This crude product was dissolved in 9 ml of acetic acid and 1 ml of water and stirred at 70° C. for 2 hours. After evaporation of the reaction solution under a reduced pressure, the residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol (90:10) to obtain a crude product. This crued product was dissolved in ethyl acetate and mixed with 4 M hydrochloric acid ethyl acetate solution, and the thus formed crystals were collected by filtration and dried to obtain 306 mg of N-(4-fluorophenyl)-N′-(1H-imidazol-4-ylmethyl)-N″-phenyl-1,3,5-triazine-2,4,6-triamine hydrochloride as colorless crystals.

후처리

  1. additionwere added
  2. temperatureAfter cooling down to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with citric acid aqueous solution and saturated brine
  5. customdried
  6. customThe solvent was evaporated under a reduced pressure
  7. washeluted with chloroform:methanol (99:1)
  8. customto obtain a crude product
  9. customAfter evaporation of the reaction solution under a reduced pressure
  10. additionthe residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was washed with saturated brine
  13. customdried
  14. customThe solvent was evaporated under a reduced pressure
  15. washeluted with chloroform:methanol (90:10)
  16. customto obtain a crude product
  17. filtrationthe thus formed crystals were collected by filtration
  18. customdried

출처 및 근거

ORD 기록
ord-0e884dc45de24d5aaf23fb4316ebc00b
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07375222B2

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