Methanol → HCID 68994470, compound

HRID 656894Notes

Reaction equation

HRID 656894 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=3)[CH:13]=[CH:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[O:23]1[C:32]2[CH:31]=[C:30]([CH:33]=O)[N:29]=[CH:28][C:27]=2[O:26][CH2:25][CH2:24]1.CO.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)(Cl)[Cl:52]>CN(C=O)C>[ClH:52].[O:23]1[C:32]2[CH:31]=[C:30]([CH2:33][NH:1][CH:2]3[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]4[C:19]5[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=5)[CH:13]=[CH:12][C:11]4=[O:22])[CH2:4][CH2:3]3)[N:29]=[CH:28][C:27]=2[O:26][CH2:25][CH2:24]1

Participants

7

Reactant 5

HCID 887MethanolHCID 6212ChloroformHCID 5049666Sodium triacetoxyborohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile

Product 1

HCID 68994470HCID 68994470, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-[2-(4-amino-1-piperidinyl)ethyl]-2-oxo-1,2-dihydro-7-quinolinecarbonitrile (300 mg, 1.01 mmol) and 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde (for a synthesis see WO2004058144, Example 2(c) or WO03/087098, Example 19(d)) (167 mg, 1.01 mmol) in chloroform (10 mL), methanol (15 mL) and DMF (20 mL) was stirred at rt for 30 min then NaBH(OAc)3 (642 mg, 3.03 mmol) was added. The reaction was stirred at rt overnight. The solvents were removed and residue dried in vacuo. The residue was subjected to column chromatography on silica gel eluting with 0-20% methanol-DCM to afford the free base of the title compound (247 mg, 55%).

Workup

  1. customThe solvents were removed
  2. customresidue dried in vacuo

Sources & evidence

ORD record
ord-4a47f63ac75c466db42f30b7e4861001
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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