1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-methyl-N-[2,2,2-trichloro-1-[(Z)-[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]ethyl]benzamide

HRID 479499노트

반응식

HRID 479499 반응식
[C:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=S)#[N:2].CCN=C=NCCCN(C)C.C(N(C(C)C)CC)(C)C.[NH2:33][CH:34]([NH:39][C:40](=[O:48])[C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)[C:35]([Cl:38])([Cl:37])[Cl:36]>CN(C=O)C.C(OCC)(=O)C>[CH3:47][C:44]1[CH:45]=[CH:46][C:41]([C:40]([NH:39][CH:34]([NH:33][C:4](=[N:3][C:1]#[N:2])[NH:6][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[C:35]([Cl:38])([Cl:36])[Cl:37])=[O:48])=[CH:42][CH:43]=1

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531Diisopropylethylamine2회HCID 18770673N-(1-amino-2,2,2-trichloroethyl)-4-methylbenzamideHCID 18770764N-cyano-N'-(3-pyridinyl)thiourea

생성물 1

HCID 1784258694-methyl-N-[2,2,2-trichloro-1-[(Z)-[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]ethyl]benzamide수율 36.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of Example 44A (200 mg, 0.932 mmol) in DMF (7 mL) at 23° C. was treated with EDCI (250 mg, 1.30 mmol) followed by diisopropyethylamine (0.180 mL, 1.03 mmol). The mixture was stirred for 30 minutes, then treated with a solution of Example 38A (262 mg, 0.932 mmol) as a solution in DMF (2 mL) along with additonal diisopropyethylamine (0.360 mL, 2.06 mmol). The solution was stirred for 10 hours, poured into ethyl acetate (25 mL), and washed with water (25 mL). The aqueous layer was extracted with ethyl acetate (20 mL), and the combined organic portions were washed with water (3×20 mL) and brine (20 mL). The organic portion was dried (Na2SO4), filtered, and concentrated. Purification of the residue by flash chromatography (elution with 5% ethanol/hexanes) provided 146 mg of the desired product as an off-white solid.

후처리

  1. stirringThe solution was stirred for 10 hours
  2. washwashed with water (25 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (20 mL)
  4. washthe combined organic portions were washed with water (3×20 mL) and brine (20 mL)
  5. dry with materialThe organic portion was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue
  9. washby flash chromatography (elution with 5% ethanol/hexanes)

출처 및 근거

ORD 기록
ord-0db2a288bafc43e3ab55640b0c826992
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645968B2

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