Diisopropylethylamine → N-[6-(4-ethylpiperazin-1-yl)pyrid-3-yl]-2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzamide

HRID 1266213노트

반응식

HRID 1266213 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:15]=2)=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:26][C:27]1[CH:28]=[CH:29][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:39][CH3:40])[CH2:35][CH2:34]2)=[N:31][CH:32]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:39]([N:36]1[CH2:35][CH2:34][N:33]([C:30]2[N:31]=[CH:32][C:27]([NH:26][C:4](=[O:5])[C:3]3[CH:7]=[C:8]([NH:11][C:12]([C:14]4[CH:19]=[CH:18][N:17]=[C:16]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[CH:15]=4)=[O:13])[CH:9]=[CH:10][C:2]=3[Cl:1])=[CH:28][CH:29]=2)[CH2:38][CH2:37]1)[CH3:40]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amineHCID 226677762-Chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzoic acid

생성물 1

HCID 9828992N-[6-(4-ethylpiperazin-1-yl)pyrid-3-yl]-2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzamide수율 28.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzoic acid (0.162 g) was added to a stirred mixture of 5-amino-2-(4-ethylpiperazin-1-yl)pyridine (0.093 g), diisopropylethylamine (0.232 g), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.176 g) and DMF (10 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with a saturated aqueous sodium bicarbonate solution and evaporated. The residue was triturated under a mixture of isohexane and ethyl acetate. The resultant solid was isolated and dried under vacuum at 40° C. to give the title compound (0.071 g); NMR Spectrum: (DMSOd6) 1.02 (t, 3H), 2.34 (m, 2H), 2.4-2.46 (m, 4H), 3.38-3.42 (m, 4H), 3.5-3.53 (m, 4H), 3.69-3.71 (m, 4H), 6.82 (d, 1H), 7.08 (d, 2H), 7.22 (s, 1H), 7.62 (d, 1H), 7.82-7.98 (m, 3H), 8.28 (d, 1H), 8.39 (s, 1H); Mass Spectrum: M+H+ 550 and 552.

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution
  3. customevaporated
  4. customThe residue was triturated under a mixture of isohexane and ethyl acetate
  5. customThe resultant solid was isolated
  6. customdried under vacuum at 40° C.

출처 및 근거

ORD 기록
ord-09e9d997cb1340d39947227223b0b68f
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06548514B1

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