(2E)-3-(4-Chlorophenyl)acryloyl chloride → (2E)-3-(4-chlorophenyl)-N-(2-piperidin-1-ylquinolin-6-yl)prop-2-enamide hydrochloride

HRID 6798

Reaction equation

HRID 6798 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27](Cl)=[O:28])=[CH:21][CH:20]=1.N1C2C(=CC(N)=CC=2)C=CC=1N>CC(O)=O.CCOCC>[ClH:18].[Cl:18][C:19]1[CH:20]=[CH:21][C:22](/[CH:25]=[CH:26]/[C:27]([NH:17][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:16]=[CH:15]3)=[O:28])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 11252649(2E)-3-(4-Chlorophenyl)acryloyl chlorideHCID 22018948Quinoline-2,6-diamineHCID 220189742-Piperidin-1-ylquinolin-6-amine

Product 1

HCID 22018962(2E)-3-(4-chlorophenyl)-N-(2-piperidin-1-ylquinolin-6-yl)prop-2-enamide hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of the product of Step D (91 mg, 0.4 mmol) in 2 mL HOAc was added the product of Step E (64 mg, 0.32 mmol). The resulting mixture was stirred at r.t. for 3 h then diluted with 3 mL ether. The resulting mixture was filtered and the resulting solids were washed with ether. The solids were dried under vacuum to afford the product, MS: m/z 392 (MH+), as an off-white solid. Using the appropriate starting materials and following procedures similar to those described above for Example 1, the following compounds were prepared from the corresponding quinoline-2,6-diamine intermediates:

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe resulting solids were washed with ether
  3. customThe solids were dried under vacuum
  4. customto afford the product, MS

Sources & evidence

ORD record
ord-7ea16d5540f64108a374fefb1059f324
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Linked notes

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