Sodium cyanoborohydride → 4-{2-[4-({[2-(2,5-Difluorophenyl)cyclopropyl]methyl}amino)piperidin-1-yl]ethyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

HRID 255224Notes

Reaction equation

HRID 255224 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]1[CH2:62][CH:61]1[CH:63]=O.C([BH3-])#N.[Na+]>>[F:52][C:53]1[CH:58]=[CH:57][C:56]([F:59])=[CH:55][C:54]=1[CH:60]1[CH2:62][CH:61]1[CH2:63][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

5

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 866426152-(2,5-Difluorophenyl)cyclopropanecarbaldehyde2×

Product 1

HCID 159838114-{2-[4-({[2-(2,5-Difluorophenyl)cyclopropyl]methyl}amino)piperidin-1-yl]ethyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrileYield 42%

Procedure

4-[2-(4-Aminopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile (Intermediate 58) (1 mmol), 2-(2,5-difluorophenyl)cyclopropanecarbaldehyde (Intermediate 68) (200 mg, 1.1 mmol) and sodium cyanoborohydride (125 mg, 2 mmol) were reacted as described under Example 21 to give 196 mg (42%) product as a gum.

Sources & evidence

ORD record
ord-55aae0bbefe441c787da463ef7cdc212
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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