Hydrochloric Acid → N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide

HRID 722410

반응식

HRID 722410 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].CCN(C(C)C)C(C)C.Cl.[NH2:31][CH2:32][CH2:33][C:34]([NH2:36])=[O:35].Cl>C(#N)C>[C:34]([CH2:33][CH2:32][NH:31][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])(=[O:35])[NH2:36]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 11460004Benzamide, N-(4-fluoro-3-nitrophenyl)-N-methyl-HCID 222222883-Aminopropanamide hydrochloride

생성물 1

HCID 21884188N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

N-(4-fluoro-3-nitro-phenyl)-N-methyl-benzamide (1.47 g, 5.37 mmol) was taken up in dry acetonitrile under argon, DIEA (2.08 g, 16.11 mmol, 2.80 ml) and β-alanine amide hydrochloride (1.00 g, 8.06 mmol) were added. The reaction mixture was heated to 80° C. for 48 h. The reaction was poured into 1N HCl and the aqueous layer was extracted 3× with ethyl acetate. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The residue was triturated twice with cold hexane and dried to give N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide. (1.75 g, 95%)

후처리

  1. extractionthe aqueous layer was extracted 3× with ethyl acetate
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe solution was filtered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was triturated twice with cold hexane
  7. customdried

출처 및 근거

ORD 기록
ord-e834417c845e47c1acbbc78398a6df70
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138420B2

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