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Methanol → HCID 68991347, compound

HRID 656901
Notes
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Reaction equation

HRID 656901 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 887MethanolHCID 6212ChloroformHCID 5049666Sodium triacetoxyborohydrideHCID 248916966,7-Dihydro-[1,4]dioxino[2,3-c]pyridazine-3-carbaldehydeHCID 68810511HCID 68810511, compound

Product 1

HCID 68991347HCID 68991347, compound
Yield 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

  1. customat rt
  2. 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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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes