Methanol → HCID 68991347, compound

HRID 656901Notes

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

Participants

Reactant 5

HCID 887Methanol

HCID 6212Chloroform

HCID 5049666Sodium triacetoxyborohydride

HCID 248916966,7-Dihydro-[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde

HCID 68810511HCID 68810511, compound

Product 1

HCID 68991347HCID 68991347, compoundYield 26%

Procedure

1-[2-(4-amino-1-piperidinyl)ethyl]-8-ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one (0.117 g, 0.368 mmol) and 6,7-dihydro[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde (0.061 g, 0.368 mmol) were dissolved in CHCl3 (2 ml) and MeOH (0.2 ml) at rt under argon. NaBH(OAc)3 (0.234 g, 1.10 mmol) was added and the reaction was allowed to stir at rt for 16 h. After which it was purified by chromatography on silica gel using a 0-30% MeOH in DCM gradient to give the free base of the title compound as a clear oil (0.045 g, 26%).

Workup

customat rt
customAfter which it was purified by chromatography on silica gel using a 0-30% MeOH in DCM gradient

Sources & evidence

ORD record: ord-54c83d94e4364410b2624899b0a0bb92
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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