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

HRID 1353472Notes

Reaction equation

HRID 1353472 reaction equation
[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

Participants

7

Reactant 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

Product 1

HCID 211016754-(2-Amino-7-chloro-4-quinolinyl)-N-[3-[(methylamino)carbonyl]cyclohexyl]-1-piperazinecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-575462f61af24223b90996cd8e5be682
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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