Diisopropylcarbodiimide → 3-(benzo[d][1,3]dioxol-5-yl)-N-(1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-yl)propanamide

HRID 2234251Notes

Reaction equation

HRID 2234251 reaction equation
CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH2:30][C:31]([OH:33])=O)=[CH:28][C:23]=2[O:22][CH2:21]1.Cl.Cl.[CH2:36]([N:43]1[C:52]2[C:47](=[CH:48][C:49]([Cl:53])=[CH:50][CH:51]=2)[CH2:46][CH:45]([NH2:54])[CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCCl>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH2:30][C:31]([NH:54][CH:45]3[CH2:46][C:47]4[C:52](=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=4)[N:43]([CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:44]3)=[O:33])=[CH:28][C:23]=2[O:22][CH2:21]1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 648103-(Benzodioxol-5-yl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 1317281071-Benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-amine, dihydrochloride

Product 1

HCID 592970333-(benzo[d][1,3]dioxol-5-yl)-N-(1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-yl)propanamideYield 9.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Typical procedure: To a suspension of PS-DIC 110 mg/well (Argonaut, 1.38 mmol/g loading) in DCE (0.5 mL) at room temperature was added HOBt (5 mg in 100 μL DMF), followed by 3-(benzo[d][1,3]dioxol-5-yl)propanoic acid (75 μmol). To this was added 1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-amine, dihydrochloride (14 mg, 50 μmol), prepared as described in Example 19C, in 1,2-dichloroethane (0.5 mL). The reaction mixture was shaken at RT for 24 h, contents were filtered into a synthesis tube rack (STR) and the solvent was dried in a speed vac. The resulting residue was chromatographed using preparative HPLC (conditions: Xterra MS-C18 (30×50 mm); eluted with 10% to 100% B, 6 min gradient. (A=100% water with 0.1% TFA and B=acetonitrile with 0.1% TFA); flow rate at 30 mL/min; UV detection at 220 nm) to give the title compound, 3-(benzo[d][1,3]dioxol-5-yl)-N-(1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-yl)propanamide, (2.2 mg, 8%). HPLC (method C): retention time=1.6 min, MS (ES): m/z 449 [M+H]+.

Workup

  1. customprepared
  2. filtrationcontents were filtered into a synthesis tube rack (STR)
  3. customthe solvent was dried in a speed vac
  4. customThe resulting residue was chromatographed
  5. washeluted with 10% to 100% B, 6 min gradient

Sources & evidence

ORD record
ord-ee02e8a8dc9d4f74a4cbc6695f3b38eb
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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