Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=O)[CH3:11])([O-])=O.NC1NN=C(C2C=CC(OC3C=CC=CC=3)=CC=2)C=1C#N.NC1C=C(C2N3N=C(C4C=CC(OC5C=CC=CC=5)=CC=4)C(C#N)=C3N=CC=2)C=CC=1.ClCCC(NC1C=C(C2[N:82]3[N:83]=[C:84]([C:89]4[CH:94]=[CH:93][C:92]([O:95][C:96]5[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=5)=[CH:91][CH:90]=4)[C:85]([C:86]([NH2:88])=[O:87])=[C:81]3[NH:80][CH2:79]C2)C=CC=1)=O>>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[N:82]2[N:83]=[C:84]([C:89]3[CH:94]=[CH:93][C:92]([O:95][C:96]4[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=4)=[CH:91][CH:90]=3)[C:85]([C:86]([NH2:88])=[O:87])=[C:81]2[NH:80][CH2:79][CH2:11]1Participants
Reactant 4
Product 1
Procedure
The desired product was prepared from 1-(2-nitrophenyl)ethanone and 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile according to the procedures similar to those for 7-(3-aminophenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (step 4 to step 5), compound 2 (step 1 and 2) and compound 68 (step 8) under appropriate conditions recognized by one of ordinary skill in the art. 1H NMR (DMSO-d6) δ 7.48-7.44 (m, 2H), 7.40-7.33 (m, 2H), 7.15-7.09 (m, 1H), 7.05-6.97 (m, 4H), 6.92 (td, J=8.0, 1.2 Hz, 1H), 6.75 (br s, 1H), 6.64 (dd, J=8.0, 1.2 Hz, 1H), 6.46 (td, J=7.6, 1.2 Hz, 1H), 6.23 (dd, J=7.6, 1.2 Hz, 1H), 5.57-5.52 (m, 1H), 5.19 (br s, 2H), 3.27-3.17 (m, 1H), 2.93 (td, J=2.8, 12.0 Hz, 1H), 2.21-2.11 (m, 1H), 2.10-2.05 (m, 1H). MS (ESI) m/e [M+1]+ 426.0.
Sources & evidence
- ORD record
- ord-00aac60d356b415e966103c34aaefaef
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447106B2
Linked notes
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