Sodium cyanoborohydride → HCID 15981895, compound

HRID 255246Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]3)[C:8]=2[CH:23]=1)(=[O:3])[CH3:2].[O:24]=[C:25]1[CH2:30][O:29][C:28]2[CH:31]=[CH:32][C:33]([CH:35]=O)=[N:34][C:27]=2[NH:26]1.C([BH3-])#N.[Na+]>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([NH:22][CH2:35][C:33]4[CH:32]=[CH:31][C:28]5[O:29][CH2:30][C:25](=[O:24])[NH:26][C:27]=5[N:34]=4)[CH2:20][CH2:21]3)[C:8]=2[CH:23]=1)(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 5003444Sodium cyanoborohydride

HCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde

HCID 667747396-Acetyl-4-[2-(4-aminopiperidin-1-yl)ethyl]-2H-1,4-benzoxazin-3(4H)-one2×

Product 1

HCID 15981895HCID 15981895, compoundYield 7%

Procedure

6-Acetyl-4-[2-(4-aminopiperidin-1-yl)ethyl]-2H-1,4-benzoxazin-3(4H)-one (Intermediate 87), 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 7% yield.

Sources & evidence

ORD record: ord-4ade39027ce648f891118e5fe75c7ee0
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875715B2

Reaction notes

Loading…