Methanol → HCID 68995468, compound

HRID 656909Notes

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](=[N:15][CH:16]=[C:17]([F:22])[C:18]=3[CH2:20][CH3:21])[CH:13]=[CH:12][C:11]2=[O:23])[CH2:4][CH2:3]1.[O:24]1[C:33]2[CH:32]=[C:31]([CH:34]=O)[N:30]=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1.CO.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)(Cl)[Cl:53]>>[ClH:53].[ClH:53].[O:24]1[C:33]2[CH:32]=[C:31]([CH2:34][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]4[C:19]5[C:14](=[N:15][CH:16]=[C:17]([F:22])[C:18]=5[CH2:20][CH3:21])[CH:13]=[CH:12][C:11]4=[O:23])[CH2:6][CH2:7]3)[N:30]=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1

Participants

Reactant 5

HCID 887Methanol

HCID 6212Chloroform

HCID 5049666Sodium triacetoxyborohydride

HCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde

HCID 68810511HCID 68810511, compound

Product 1

HCID 68995468HCID 68995468, compoundYield 48%

Procedure

1-[2-(4-amino-1-piperidinyl)ethyl]-8-ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one (0.056 g, 0.184 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)) (0.030 g, 0.184 mmol) was dissolved in CHCl3 (1 ml) and MeOH (0.1 ml) at rt under argon. NaBH(OAc)3 (0.117 g, 0.552 mmol) was then added and the reaction was allowed to stir at rt for 16 h. After which it was purified by chromatography on silica gel (10 g) using a 0-30% MeOH in DCM gradient to give the free base of the title compound as a yellow oil (0.041 g, 48%).

Workup

customat rt
customAfter which it was purified by chromatography on silica gel (10 g)

Sources & evidence

ORD record: ord-491c5e575b9147d18699e30b5a736b6e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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