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Methylamine → 4-(2-Amino-7-chloro-4-quinolinyl)-N-[3-[(methylamino)carbonyl]cyclohexyl]-1-piperazinecarboxamide

HRID 1353472
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HRID 1353472 반응식
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27](O)=[O:28])[CH2:22]3)=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:30])=[CH:7][CH:8]=2)[N:3]=1.[CH3:31][N:32](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([NH:32][CH3:31])=[O:28])[CH2:22]3)=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:30])=[CH:7][CH:8]=2)[N:3]=1
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참가 물질

7

반응물 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 211015923-[[[4-(2-Amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acid

생성물 1

HCID 21101675
4-(2-Amino-7-chloro-4-quinolinyl)-N-[3-[(methylamino)carbonyl]cyclohexyl]-1-piperazinecarboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

The mixture of 3-[[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acid (30 mg, 0.069 mmol), HATU (100 mg), methylamine (1.0M in THF, 3 mL) and diisopropylethylamine (0.5 mL) in DMF (3 mL) was stirred at rt for 3 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with sat. NaHCO3 solution and water, and dried over Na2SO4. Concentration in vacuo followed by flash chromatography afforded the title product. LC-MS: 445 (M++1). 1H NMR (CD3OD) δ 1.10–1.35 (m, 4H), 1.65–1.90 (m, 4H), 2.20 (m, 1H), 2.65 (s, 3H), 3.08 (m, 4H), 3.60 (m, 5H), 5.80 (d, 1H), 6.15 (s, 1H), 7.10 (d, 2H), 7.45 (s, 1H), 7.65 (a, 1H).

후처리

  1. washwashed with sat. NaHCO3 solution and water
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-575462f61af24223b90996cd8e5be682
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07220856B2

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