Sodium cyanoborohydride → 4-[2-(4-{[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]amino}piperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

HRID 255230Notes

Reaction equation

HRID 255230 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]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[O:13][CH2:12][C:11]2=[O:22])[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.NC1CCN(CCN2C3C=C(C#N)C=CC=3OCC2=O)CC1.[F:52][C:53]1[CH:58]=[CH:57][C:56]([F:59])=[CH:55][C:54]=1/[CH:60]=[CH:61]/[CH:62]=O.C([BH3-])#N.[Na+]>ClCCl.CO>[F:52][C:53]1[CH:58]=[CH:57][C:56]([F:59])=[CH:55][C:54]=1/[CH:60]=[CH:61]/[CH2:62][NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:15]3[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[O:13][CH2:12][C:11]2=[O:22])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 667749874-[2-(4-aminopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrileHCID 667750584-[2-(4-Aminopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile trifluoroacetateHCID 86642138(2E)-3-(2,5-difluorophenyl)-2-propenal

Product 1

HCID 119832164-[2-(4-{[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]amino}piperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrileYield 30.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-[2-(4-Aminopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile (Intermediate 58) (1.5 mmol), (2E)-3-(2,5-difluorophenyl)acrylaldehyde (202 mg, 1.2 mmol) (FR 2872164) (200 mg, 1.1 mmol) and sodium cyanoborohydride were reacted as described under Example 21. Chromatography on silica gel with dichloromethane/methanol gave 168 mg (25%) product

Sources & evidence

ORD record
ord-4f814522884d474ead72cafd4c79cdbe
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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