8-Amino-9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino-[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrile → 10-(3-(1H-pyrazol-1-yl)propylamino)-8-amino-9-fluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrile

HRID 444797Notes

Reaction equation

HRID 444797 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]2[O:14][CH2:15][C:16]3([CH2:18][CH2:17]3)[N:7]3[C:8]=2[C:3]=1[C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6]3.[NH:22]1[CH:26]=[CH:25][C:24](CCCN)=[N:23]1>>[N:23]1([CH2:4][CH2:3][CH2:2][NH:1][C:10]2[C:9]3[O:14][CH2:15][C:16]4([CH2:17][CH2:18]4)[N:7]4[C:8]=3[C:3]([C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6]4)=[C:2]([NH2:1])[C:11]=2[F:12])[CH:24]=[CH:25][CH:26]=[N:22]1

Participants

3

Reactant 2

HCID 581346818-Amino-9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino-[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrileHCID 1785109273-(1H-Pyrazol-3-yl)propan-1-amine

Product 1

HCID 5813464110-(3-(1H-pyrazol-1-yl)propylamino)-8-amino-9-fluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrile

Procedure

The title compound was prepared from 8-amino-9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1′-cyclopropane]-6-carbonitrile and pyrazolepropylamine using synthetic procedures similar to those described in the examples above. 1H-NMR (400 MHz, DMSO-d6) δ 1.16 (2H, t), 1.58 (2H, t), 1.99 (2H, m), 3.65 (2H, m), 4.16 (2H, s), 4.26 (2H, m), 6.29 (1H, s), 7.49 (1H, s), 7.63 (1H, s), 8.04 (1H, s). MS (EP) m/z: 395 (M++1). (Calcd for C20H19FN6O2, 394.40).

Sources & evidence

ORD record
ord-18c60574eabf435c929dab81ef4cb87b
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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