Sodium cyanoborohydride → 6-Bromo-4-[2-(4-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}piperidin-1-yl)ethyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1644357Notes

Reaction equation

HRID 1644357 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:15](=[O:16])[CH2:14][O:13][C:12]3[CH:17]=[CH:18][C:19]([Br:21])=[N:20][C:11]2=3)[CH2:4][CH2:3]1.[O:22]=[C:23]1[CH2:28][O:27][C:26]2[CH:29]=[CH:30][C:31]([CH:33]=O)=[N:32][C:25]=2[NH:24]1.C([BH3-])#N.[Na+]>>[Br:21][C:19]1[CH:18]=[CH:17][C:12]2[O:13][CH2:14][C:15](=[O:16])[N:10]([CH2:9][CH2:8][N:5]3[CH2:6][CH2:7][CH:2]([NH:1][CH2:33][C:31]4[CH:30]=[CH:29][C:26]5[O:27][CH2:28][C:23](=[O:22])[NH:24][C:25]=5[N:32]=4)[CH2:3][CH2:4]3)[C:11]=2[N:20]=1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 866426194-[2-(4-Aminopiperidin-1-yl)ethyl]-6-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one2×

Product 1

HCID 159818906-Bromo-4-[2-(4-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}piperidin-1-yl)ethyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 64%

Procedure

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Intermediate 79), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) and sodium cyanoborohydride were reacted as described under Example 21 to give the product as an off-white solid in 64% yield.

Sources & evidence

ORD record
ord-44adee8e1c41486daeb09fe6eedcd790
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

Loading…