1-(Aminooxy)-2-methyl-2-propanol → 1-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxy-2-methylpropan-2-ol
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22](=O)[CH3:23])[N:20]=2)[N:15]=[N:14]1.[NH2:25][O:26][CH2:27][C:28]([CH3:31])([OH:30])[CH3:29]>>[OH:30][C:28]([CH3:31])([CH3:29])[CH2:27][O:26]/[N:25]=[C:22](/[C:19]1[N:20]=[C:21]2[N:13]([CH2:12][C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[F:1])[N:9]=[CH:8][CH:7]=[CH:6]4)[N:14]=[N:15][C:16]2=[N:17][CH:18]=1)\[CH3:23]Participants
3
Procedure
The title compound (12.0 mg, 89%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (15.4) (10.0 mg, 0.03 mmol) and 1-aminooxy-2-methyl-propan-2-ol (6.5 mg, 0.06 mmol) using the same procedure as described in the synthesis of example 15. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.29 (s, 1H), 8.93 (dd, 1H), 8.41 (dd, 1H), 8.19 (d, 1H), 7.83 (d, 1H), 7.54 (dd, 1H), 6.23 (s, 2H), 4.60 (s, 1H), 4.12 (d, 2H), 2.30 (s, 3H), 1.17 (s, 6H). LCMS (method A): [MH]+=410, tR=5.40 min.
Workup
- customas described in the synthesis of example 15
Sources & evidence
- ORD record
- ord-a394950184f9444faedb0a49bb1b164a
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507676B2
Reaction notes
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