Cyclopropanecarboxaldehyde → 4-(6-Bromo-2-cyclopropyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine

HRID 1398695노트

반응식

HRID 1398695 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[N:15]=[C:14]([NH2:16])[N:13]=[CH:12][N:11]=1.[CH:17]1([CH:20]=O)[CH2:19][CH2:18]1.OOS([O-])=O.[K+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:20]([CH:17]3[CH2:19][CH2:18]3)[N:9]([C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:16])[N:15]=3)[C:3]=2[CH:4]=1

참가 물질

6

반응물 4

HCID 123114CyclopropanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 681816982-N-(2-amino-5-bromophenyl)-1,3,5-triazine-2,4-diamine

생성물 1

HCID 681815764-(6-Bromo-2-cyclopropyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-N-(2-amino-5-bromophenyl)-1,3,5-triazine-2,4-diamine (6 g, 21.34 mmol) in DMF (60 mL) was added cyclopropanecarbaldehyde (2.07 ml, 27.75 mmol) followed by oxone (7.83 g, 12.81 mmol). The reaction mixture was stirred at RT for 24 hr. The reaction mixture was then cooled to 0° C. and saturated aqueous sodium bicarbonate introduced. A brown precipitate was removed by vacuum filtration. The solid was washed with DCM (100 ml). The organic phase of the filtrate was separated and the aqueous phase extracted with DCM (2×100 mL extractions). The combined organics were washed with brine and then dried (Na2SO4), filtered and concentrated in vacuo to furnish the crude title compound as a brown solid: 1H NMR (500 MHz, DMSO) delta 1.32-1.02 (4H, m), 7.41 (1H, dd, J=8.5, 1.9 Hz), 7.50 (1H, d, J=8.5), 8.05 (1H, s), 8.11 (1H, s), 8.49 (1H, d, J=1.8 Hz), 8.66 (1H, s); LC-MS: m/z=+330.90 (M+H)+. This compound of 85% purity LC-MS (UV) was used without further purification.

후처리

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customA brown precipitate was removed by vacuum filtration
  3. washThe solid was washed with DCM (100 ml)
  4. customThe organic phase of the filtrate was separated
  5. extractionthe aqueous phase extracted with DCM (2×100 mL extractions)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9db5c66a416a4550971e802a835b2e69
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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