Benzaldehyde → HCID 44540662, compound

HRID 402575Notes

Reaction equation

HRID 402575 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[N:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[C:12]3[O:20][C:21]([CH3:25])([CH3:24])[O:22][CH2:23][C:11]=23)=[CH:4][CH:3]=1.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([BH3-])#N.[Na+]>>[CH2:26]([N:8]([CH2:9][C:10]1[CH:15]=[N:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[C:12]2[O:20][C:21]([CH3:25])([CH3:24])[O:22][CH2:23][C:11]=12)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58360284HCID 58360284, compound

Product 1

HCID 44540662HCID 44540662, compound

Procedure

Methyl 5-((benzyl(4-fluorophenyl)amino)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate 25a was prepared from methyl 5-((4-fluorophenylamino)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate (21a) (120 mg, 0.3 mmol), benzaldehyde (100 uL, 1.0 mmol) and sodium cyanoborohydride (28 mg, 0.45 mmol) according to the procedure described in Example 24. MS-ESI m/z 437 [MH]+.

Sources & evidence

ORD record
ord-af8166d615f0412a88a69aac5d5b7a77
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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