2-Methoxy-4-(4-methyl-piperazin-1-yl)-benzaldehyde → HCID 178493012, compound

HRID 591978Notes

Reaction equation

HRID 591978 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[CH:5]=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]2)[CH:27]=[CH:26][C:23]=1[CH:24]=O>>[CH3:20][O:21][C:22]1[CH:29]=[C:28]([N:30]2[CH2:31][CH2:32][N:33]([CH3:36])[CH2:34][CH2:35]2)[CH:27]=[CH:26][C:23]=1[C:24]1[NH:1][C:2]2=[N:3][CH:4]=[CH:5][C:6]([NH:9][C@@H:10]3[C@@H:15]4[CH2:16][C@@H:12]([CH:13]=[CH:14]4)[C@@H:11]3[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=1

Participants

3

Reactant 2

HCID 840082152-Methoxy-4-(4-methyl-piperazin-1-yl)-benzaldehydeHCID 117701640(1S,2S,3R,4R)-3-(2,3-Diamino-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178493012HCID 178493012, compoundYield 21%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50.0 mg, 0.193 mmol) and 2-methoxy-4-(4-methyl-piperazin-1-yl)-benzaldehyde (49.7 mg, 0.212 mmol) were reacted to produce 19 mg (21%) of the title compound. mp: 185-195° C., 1H NMR (300 MHz, DMSO-d6): 11.87 (s, 1H), 8.01 (s, 1H), 7.87 (s, 1H), 7.65 (s, 1H), 7.16 (s, 1H), 6.73 (m, 1H), 6.68 (s, 1H), 6.60 (s, 1H), 6.37 (s, 1H), 6.32 (s, 2H), 3.95 (s, 4H), 2.86 (s, 1H), 2.75 (s, 1H), 2.24 (s, 4H), 1.42 (s, 1H), 1.24 (s, 1H). MS: 474 (M+H), HPLC: 1.59 min (G method).

Sources & evidence

ORD record
ord-e016be8725e348c7b2fdade7bef21041
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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