2-Methoxy-4-(4-morpholin-4-yl-piperidin-1-yl)-benzaldehyde → HCID 178492999, compound

HRID 591933Notes

Reaction equation

HRID 591933 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][O:81][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[CH2:73][CH2:74][CH:75]([N:78]5[CH2:83][CH2:82][O:81][CH2:80][CH2:79]5)[CH2:76][CH2:77]4)=[CH:71][C:64]=3[O:63][CH3:62])[NH:42][C:43]2=[N:44][CH:45]=1

Participants

4

Reactant 3

HCID 1177018152-Methoxy-4-(4-morpholin-4-yl-piperidin-1-yl)-benzaldehydeHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideHCID 178513995HCID 178513995, compound

Product 1

HCID 178492999HCID 178492999, compoundYield 75%

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-morpholin-4-yl-piperidin-1-yl)-benzaldehyde were reacted to produce the title compound (75%). 1H NMR (d-6 DMSO): 12.50 (br s, 1H), 9.85 (br s, 1H), 8.09 (s, 1H), 8.04 (d, J=9 Hz, 1H), 7.83 (br s, 1H), 7.29 (s, 1H), 6.77 (d, J=9 Hz, 1H), 6.66 (s, 1H), 6.38 (s, 2H), 5.15 (m, 1H), 3.95-4.30 (m, 7H), 3.69 (t, J=10 Hz, 2H), 3.48 (m, 3H), 3.13 (m, 2H), 2.82-2.96 (m, 4H), 2.63 (d, J=8 Hz, 1H), 2.11-2.26 (m, 3H), 2.08 (s, 1H), 1.69 (m, 2H), 1.41 (d, J=9 Hz, 1H). MS: 579.20 (M+H). HPLC retention time: 1.91 minutes (G Method).

Sources & evidence

ORD record
ord-36ec7056183b475b9832a54936f9557f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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