4-(2-(4-Methylpiperazin-1-yl)-2-oxoethoxy)benzaldehyde → HCID 178481077, compound

HRID 592085Notes

Reaction equation

HRID 592085 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])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:39])[CH2:29][O:30][C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)[CH2:24][CH2:23]1>>[Cl:20][C:5]1[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])=[C:7]2[N:8]=[C:35]([C:34]3[CH:33]=[CH:32][C:31]([O:30][CH2:29][C:28]([N:25]4[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]4)=[O:39])=[CH:38][CH:37]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 283794934-(2-(4-Methylpiperazin-1-yl)-2-oxoethoxy)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 amide

Product 1

HCID 178481077HCID 178481077, compoundYield 26%

Procedure

(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (1 eq.) and 4-(2-(4-methylpiperazin-1-yl)-2-oxoethoxy)benzaldehyde (58) (1.1 eq) were reacted in an analogous manner as compound CCXXIII to yield the desired product (26%) as an off white solid. NMR: δ (1H, 400 MHz, DMSO-d6): 1.38 (1H, d, J=8 Hz), 2.19 (3H, s), 2.20-2.35 (5H, m), 2.62 (1H, d, J=8.4 Hz), 2.78 (1H, s), 2.89 (1H, s), 3.40-3.50 (4H, m), 4.91 (2H, s), 5.16 (1H, t, J=8 Hz), 6.36-6.40 (2H, m), 7.08 (2H, d, J=8.4 Hz), 7.11-7.14 (1H, m), 7.22 (1H, bs), 7.76 (1H, bs), 7.92 (1H, s), 8.05 (2H, d, J=8.4 Hz).

Sources & evidence

ORD record
ord-790d5d271be6445da07b825568aba083
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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