Dichloromethane → 1-[2-((3S,4S)-3-{[(6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)amino]methyl}-4-hydroxy-1-pyrrolidinyl)ethyl]-7-(methyloxy)-2(1H)-quinolinone hydrochloride

HRID 657039Notes

Reaction equation

HRID 657039 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:7]([OH:8])[CH2:6][N:5]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:23])[CH2:4]1.[N:24]1[C:29]2[O:30][CH2:31][CH2:32][O:33][C:28]=2[CH:27]=[C:26]([CH:34]=O)[N:25]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:57]>CO>[ClH:57].[N:24]1[C:29]2[O:30][CH2:31][CH2:32][O:33][C:28]=2[CH:27]=[C:26]([CH2:34][NH:1][CH2:2][C@@H:3]2[C@H:7]([OH:8])[CH2:6][N:5]([CH2:9][CH2:10][N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[CH:14]=[CH:13][C:12]3=[O:23])[CH2:4]2)[N:25]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 248916966,7-Dihydro-[1,4]dioxino[2,3-c]pyridazine-3-carbaldehydeHCID 688094001-{2-[(3S,4S)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-2(1H)-quinolinone

Product 1

HCID 689932981-[2-((3S,4S)-3-{[(6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)amino]methyl}-4-hydroxy-1-pyrrolidinyl)ethyl]-7-(methyloxy)-2(1H)-quinolinone hydrochlorideYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{2-[(3S,4S)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-2(1H)-quinolinone (118 mg, 0.372 mmol) and 6,7-dihydro[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde (68 mg, 0.409 mmol) were combined in anhydrous DCM (5 ml) and anhydrous MeOH (1 ml) with a spatula of solid sodium carbonate. The reaction mixture was stirred under nitrogen for 18 h then sodium triacetoxyborohydride (247 mg, 1.12 mmol) was added and stirred for 1 h. The reaction mixture was concentrated and purified to obtain the free base of the title compound as a pale oil (35 mg, 20%) after column:chromatography (90:10:1: DCM:MeOH:NH4OH).

Workup

  1. stirringstirred for 1 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified

Sources & evidence

ORD record
ord-3192975769a746d2a3deff8c64d1c2bd
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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