Sodium triacetoxyborohydride → HCID 15983305, compound

HRID 255175Notes

Reaction equation

HRID 255175 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](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=3)[CH:13]=[CH:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[O:23]=[C:24]1[CH2:29][O:28][C:27]2[CH:30]=[CH:31][C:32]([CH:34]=O)=[N:33][C:26]=2[NH:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[O:22]=[C:11]1[CH:12]=[CH:13][C:14]2[C:19](=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:10]1[CH2:9][CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][CH2:34][C:32]2[CH:31]=[CH:30][C:27]3[O:28][CH2:29][C:24](=[O:23])[NH:25][C:26]=3[N:33]=2)[CH2:3][CH2:4]1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile2×

Product 1

HCID 15983305HCID 15983305, compound

Procedure

1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile (Intermediate 14, 70 mg, 0.24 mmol), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (42 mg, 0.24 mmol)and sodium triacetoxy borohydride (150 mg, 0.75 mmol) were reacted as described for Example 5. Chromatography on silica gel with dichloromethane/methanol (6:1) and crystallization from ethyl acetate/hexanes gave the product as a colorless solid, 73 mg (67%), mp 212° C.

Workup

  1. customChromatography on silica gel with dichloromethane/methanol (6:1) and crystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-edd8d8f6b3f04702ba61a69d6a5c25ca
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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