2-Methoxy-4-(4-methyl-piperazin-1-yl)-benzaldehyde → HCID 178493011, compound

HRID 591932Notes

Reaction equation

HRID 591932 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].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][N:75]([CH3:78])[CH2:74][CH2:73]2)[CH:69]=[CH:68][C:65]=1[CH:66]=O>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[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][N:75]([CH3:78])[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 840082152-Methoxy-4-(4-methyl-piperazin-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 178493011HCID 178493011, compoundYield 62%

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-methyl-piperazin-1-yl)-benzaldehyde were reacted to produce the title compound (62%). 1H NMR (d-chloroform): 13.76 (br s, 1H), 8.21 (d, J=8 Hz, 1H), 7.97 (d, J=8 Hz, 1H), 7.80 (s, 1H), 6.62 (d, J=8 Hz, 1H), 6.47 (s, 1H), 6.46 (m, 1H), 6.42 (br s, 1H), 6.07 (br s, 1H), 5.40 (t, J=9 Hz, 1H), 4.11 (s, 3H), 3.65-3.90 (m, 4H), 3.40-3.60 (m, 2H), 3.16 (s, 1H), 3.03 (m, 1H), 2.99 (s, 1H), 2.92 (s, 3H), 2.72) d, J=8 Hz, 1H), 2.32 (d, J=9 Hz, 1H), 1.80-2.10 (m, 2H), 1.68 (d, J=9 Hz, 1H). MS: 509.14 (M+H). HPLC retention time: 1.82 minutes (G Method).

Sources & evidence

ORD record
ord-d90f85f15ea647eea745f99c7e43d562
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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