2-Methoxy-4-(trifluoromethoxy)benzaldehyde → HCID 178493549, compound

HRID 591930Notes

Reaction equation

HRID 591930 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]([O:72][C:73]([F:76])([F:75])[F:74])[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]([O:72][C:73]([F:74])([F:75])[F:76])=[CH:71][C:64]=3[O:63][CH3:62])[NH:42][C:43]2=[N:44][CH:45]=1

Participants

4

Reactant 3

HCID 37238252-Methoxy-4-(trifluoromethoxy)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 178493549HCID 178493549, 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-trifluoromethoxy-benzaldehyde were reacted to produce the title compound (60%). 1H NMR (d-chloroform): 13.94 (br s, 1H), 8.31 (d, J=9 Hz, 1H), 8.20 (d, J=9 Hz, 1H), 7.83 (s, 1H), 6.97 (d, J=9 Hz, 1H), 6.82 (s, 1H), 6.44 (m, 2H), 6.24 (s, 1H), 5.82 (s, 1H), 5.35 (d, J=9 Hz, 1H), 4.11 (s, 3H), 3.17 (s, 1H), 2.97 (s, 1H), 2.74 (d, J=8 Hz, 1H), 2.31 (d, J=9 Hz, 1H), 1.65 (d, J=9 Hz, 1H). MS: 495.00 (M+H). HPLC retention time: 3.12 minutes (G Method).

Sources & evidence

ORD record
ord-63be95b8981b4601be62fecbf7b5adc1
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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