4-(4-Methylpiperazin-1-yl)benzaldehyde → (1S,2S,3R,4R)-3-{6-Chloro-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-imidazo[4,5-b]pyridine-7-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide trifluoroacetic acid salt

HRID 591924Notes

Reaction equation

HRID 591924 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[C:10]([NH:31][C@@H:32]2[C@@H:37]3[CH2:38][C@@H:34]([CH:35]=[CH:36]3)[C@@H:33]2[C:39]([NH2:41])=[O:40])=[C:11]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21](CN4CCOCC4)=[CH:20][CH:19]=3)[NH:15][C:12]2=[N:13][CH:14]=1.NC1C(N)=C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)C(Cl)=CN=1.[CH3:62][N:63]1[CH2:68][CH2:67][N:66](C2C=CC(C=O)=CC=2)[CH2:65][CH2:64]1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[C:10]([NH:31][C@@H:32]2[C@@H:37]3[CH2:38][C@@H:34]([CH:35]=[CH:36]3)[C@@H:33]2[C:39]([NH2:41])=[O:40])=[C:11]2[N:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([N:66]4[CH2:67][CH2:68][N:63]([CH3:62])[CH2:64][CH2:65]4)=[CH:22][CH:23]=3)[NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 7365334-(4-Methylpiperazin-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 178480652(1S,2S,3R,4R)-3-{6-Chloro-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-imidazo[4,5-b]pyridine-7-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide trifluoroacetic acid saltYield 88%

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 4-(4-Methyl-piperazin-1-yl)-benzaldehyde were reacted to produce the title compound (88%). 1H NMR (d-chloroform): 15.58 (br s, 1H) 8.36 (d, J=9 Hz, 1H), 8.00 (d, J=9 Hz, 2H), 7.78 (s, 1H), 7.02 (d, J=9 Hz, 2H), 6.48 (m, 1H), 6.41 (m, 1H), 5.99 (s, 1H), 5.61 (s, 1H), 5.35 (t, J=9 Hz, 1H), 3.38-3.93 (m, 8H), 3.17 (s, 1H), 3.04 (m, 1H), 3.02 (s, 1H), 2.91 (s, 3H), 2.69 (d, J=9 Hz, 1H), 2.31 (d, J=9 Hz, 1H), 1.67 (d, J=9 Hz, 1H). MS: 479.11 (M+H). HPLC retention time: 1.81 minutes (G Method).

Sources & evidence

ORD record
ord-2d48e57c0807463799304ae3de835d9a
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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