Sodium cyanoborohydride → HCID 15983552, compound

HRID 255208Notes

Reaction equation

HRID 255208 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]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=3[S:13][CH2:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[O:23]1[C:32]2[CH:31]=[C:30]([CH:33]=O)[N:29]=[CH:28][C:27]=2[O:26][CH2:25][CH2:24]1.C([BH3-])#N.[Na+]>>[O:23]1[C:32]2[CH:31]=[C:30]([CH2:33][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]4[C:15]5[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=5[S:13][CH2:12][C:11]4=[O:22])[CH2:6][CH2:7]3)[N:29]=[CH:28][C:27]=2[O:26][CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 667745334-[2-(4-Aminopiperidin-1-yl)ethyl]-6-methoxy-2H-1,4-benzothiazin-3(4H)-one2×

Product 1

HCID 15983552HCID 15983552, compoundYield 13%

Procedure

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-methoxy-2H-1,4-benzothiazin-3(4H)-one (Intermediate 50) (0.9 mmol), 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (WO 2004/058144) (180 mg, 1.1 mmol), and sodium cyanoborohydride (110 mg, 1.76 mmol) were reacted as described under Example 21 to give 55 mg (13%) product as a dry film.

Sources & evidence

ORD record
ord-f547886294024b6e90aa6ddc63cdb3c9
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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