1-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxy-1,4-dihydro-2H-3,1-benzoxazin-2-one trifluoro acetate → 4-[2-(4-Amino-2-oxopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

HRID 255279Notes

Reaction equation

HRID 255279 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][C:16]3=[O:29])[C:7]=2[CH:30]=1)#[N:2].FC(F)(F)C(O)=O.NC1CCN(CCN2C3C=C(OC)C=CC=3COC2=O)CC1>>[NH2:21][CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:8]2[C:7]3[CH:30]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[O:11][CH2:10][C:9]2=[O:12])[C:16](=[O:29])[CH2:17]1

Participants

3

Reactant 2

HCID 667737611-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxy-1,4-dihydro-2H-3,1-benzoxazin-2-one trifluoro acetateHCID 86642634tert-Butyl {1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-2-oxopiperidin-4-yl}carbamate2×

Product 1

HCID 667740114-[2-(4-Amino-2-oxopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

Procedure

tert-Butyl {1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-2-oxopiperidin-4-yl}carbamate (Intermediate 117, 225 mg, 0.54 mmol) was reacted as described for Intermediate 106. The crude trifluoro acetate of the title compound was obtained as a red oil, 232 mg (quantitative), and used without further purification for the next step.

Sources & evidence

ORD record
ord-a09af52d587448f5a8dae02e22af5ffe
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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