Sodium cyanoborohydride → HCID 15982149, compound

HRID 255262Notes

Reaction equation

HRID 255262 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:15]3[CH:16]=[C:17]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:18]=[CH:19][C:14]=3[O:13][CH2:12][C:11]2=[O:24])[CH2:4][CH2:3]1.[O:25]=[C:26]1[CH2:31][O:30][C:29]2[CH:32]=[CH:33][C:34]([CH:36]=O)=[N:35][C:28]=2[NH:27]1.C([BH3-])#N.[Na+]>>[CH3:23][S:20]([C:17]1[CH:18]=[CH:19][C:14]2[O:13][CH2:12][C:11](=[O:24])[N:10]([CH2:9][CH2:8][N:5]3[CH2:6][CH2:7][CH:2]([NH:1][CH2:36][C:34]4[CH:33]=[CH:32][C:29]5[O:30][CH2:31][C:26](=[O:25])[NH:27][C:28]=5[N:35]=4)[CH2:3][CH2:4]3)[C:15]=2[CH:16]=1)(=[O:22])=[O:21]

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 66775170HCID 66775170, compound2×

Product 1

HCID 15982149HCID 15982149, compoundYield 8%

Procedure

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-(methylsulfonyl)-2H-1,4-benzoxazin-3(4H)-one (Intermediate 99), 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 8% yield.

Sources & evidence

ORD record
ord-3ddc630e8f104b509ff510a394c07483
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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