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

HRID 479499ノート

反応式

HRID 479499 の反応式
[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

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531Diisopropylethylamine2 回HCID 18770673N-(1-amino-2,2,2-trichloroethyl)-4-methylbenzamideHCID 18770764N-cyano-N'-(3-pyridinyl)thiourea

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0db2a288bafc43e3ab55640b0c826992
出典データセット
uspto-grants-2003_11
特許番号
US06645968B2

反応ノート

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