HCID 89726145, compound → HCID 178492995, compound

HRID 591934Notes

Reaction equation

FC(F)(F)C(O)=O.ClC1C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)=C2N=C(C3C=CC(CN4CCOCC4)=CC=3)NC2=NC=1.[NH2:42][C:43]1[C:48]([NH2:49])=[C:47]([NH:50][C@@H:51]2[C@@H:56]3[CH2:57][C@@H:53]([CH:54]=[CH:55]3)[C@@H:52]2[C:58]([NH2:60])=[O:59])[C:46]([Cl:61])=[CH:45][N:44]=1.[CH3:62][O:63][C:64]1[CH:71]=[C:70]([N:72]2[CH2:77][CH2:76][CH:75]([N:78]3[CH2:83][CH2:82][N:81]([CH3:84])[CH2:80][CH2:79]3)[CH2:74][CH2:73]2)[CH:69]=[CH:68][C:65]=1[CH:66]=O>>[Cl:61][C:46]1[C:47]([NH:50][C@@H:51]2[C@@H:56]3[CH2:57][C@@H:53]([CH:54]=[CH:55]3)[C@@H:52]2[C:58]([NH2:60])=[O:59])=[C:48]2[N:49]=[C:66]([C:65]3[CH:68]=[CH:69][C:70]([N:72]4[CH2:77][CH2:76][CH:75]([N:78]5[CH2:79][CH2:80][N:81]([CH3:84])[CH2:82][CH2:83]5)[CH2:74][CH2:73]4)=[CH:71][C:64]=3[O:63][CH3:62])[NH:42][C:43]2=[N:44][CH:45]=1

Participants

Reactant 3

HCID 89726145HCID 89726145, compound

HCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HCID 178513995HCID 178513995, compound

Product 1

HCID 178492995HCID 178492995, compoundYield 60%

Procedure

In the same fashion as for Compound III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 2-Methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-benzaldehyde were reacted to produce the title compound (60%). 1H NMR (d-chloroform): 10.62 (br s, 1H), 8.22 (d, J=9 Hz, 1H), 7.98 (s, 1H), 6.66 (m, 2H), 6.50 (s, 1H), 6.33 (d, J=10 Hz, 2H), 5.07-5.19 (m, 2H), 4.03 (s, 3H), 3.90 (d, J=11 Hz, 2H), 3.49 (s, 2H), 3.17 (s, 1H), 2.89 (m, 4H), 2.65 (m, 4H), 2.46 (m, 4H), 232 (m, 1H), 2.31 (s, 3H), 1.97 (d, J=11 Hz, 2H), 1.60-1.79 (m, 3H). MS: 592.22 (M+H). HPLC retention time: 1.76 minutes (G Method).

Sources & evidence

ORD record: ord-d07069c82dbd4864a76e341c74799496
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

Loading…