HCID 57036484, compound → HCID 178438901, compound

HRID 591953Notes

Reaction equation

HRID 591953 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.[CH2:21]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[C:26]([O:32][CH3:33])[CH:25]=1)[CH:22]=[CH2:23]>>[CH2:21]([C:24]1[CH:31]=[CH:30][C:27]([C:28]2[NH:1][C:2]3=[N:3][CH:4]=[C:5]([Cl:20])[C:6]([NH:9][C@@H:10]4[C@@H:15]5[CH2:16][C@@H:12]([CH:13]=[CH:14]5)[C@@H:11]4[C:17]([NH2:19])=[O:18])=[C:7]3[N:8]=2)=[C:26]([O:32][CH3:33])[CH:25]=1)[CH:22]=[CH2:23]

Participants

3

Reactant 2

HCID 57036484HCID 57036484, compoundHCID 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 178438901HCID 178438901, compoundYield 12%

Procedure

In a similar fashion as for the synthesis of 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-allyl-2-methoxybenzaldehyde were reacted to produce the title compound as a yellow solid (12%). Mp. 123-6° C. 1H NMR (d-chloroform): 10.83 (br s, 1H), 8.32 (d, J=8 Hz, 1H), 8.02 (s, 1H), 7.00 (d, J=7 Hz, 1H), 6.91 (s, 1H), 6.46-6.31 (m, 3H), 6.00 (m, 1H), 5.55 (d, J=10 Hz, 1H), 5.28-5.12 (m, 4H), 4.05 (s, 3H), 3.48 (d, J=7 Hz, 1H), 3.18 (s, 1H), 2.91 (s, 1H), 2.87 (d. J=7 Hz, 1H), 2.35 (d, J=8 Hz, 1H), 1.75 (d, J=8 Hz, 1H). MS: 449.9 (M+H). HPLC retention time: 2.94 minutes (G Method).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e00b90cfab5d445fbf59cbc5a150104f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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