Ethyl 6-cyclopropylpyrazine-2-carbimidate → HCID 178521016, compound

HRID 931213Notes

Reaction equation

HRID 931213 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)=[N:8][C:9]=1[NH2:10].Cl.Cl.NC1C=CC(N2CCC[C@@H](C(N3CCCC3)=O)C2)=NC=1N.NC1N=C(N2CCC[C@@H](C(N3CCOCC3)=O)C2)C=CC=1[N+]([O-])=O.[CH:72]1([C:75]2[N:80]=[C:79]([C:81](=N)OCC)[CH:78]=[N:77][CH:76]=2)[CH2:74][CH2:73]1>>[CH:72]1([C:75]2[N:80]=[C:79]([C:81]3[NH:10][C:9]4=[N:8][C:7]([N:11]5[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]6[CH2:20][CH2:21][O:22][CH2:23][CH2:24]6)=[O:18])[CH2:12]5)=[CH:6][CH:5]=[C:4]4[N:3]=3)[CH:78]=[N:77][CH:76]=2)[CH2:74][CH2:73]1

Participants

5

Reactant 4

HCID 89853280Ethyl 6-cyclopropylpyrazine-2-carbimidateHCID 89853875(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(morpholino)methanone dihydrochlorideHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochlorideHCID 117966273(R)-(1-(6-Amino-5-nitropyridin-2-yl)piperidin-3-yl)(morpholino)methanone

Product 1

HCID 178521016HCID 178521016, compound

Procedure

The title compound was prepared by a method analogous to the one used for Example 95, but using (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(morpholino)methanone dihydrochloride (synthesized by hydrogenation analogous to the one used for Intermediate 1, starting from Intermediate 40) and Intermediate 30. 1H NMR (300 MHz, DMSO-d6) δ 1.06 (dd, 2H), 1.20-1.33 (m, 3H), 1.54-1.74 (m, 3H), 1.80-1.93 (m, 1H), 2.19-2.33 (m, 2H), 2.79 (br s, 1H), 2.87-3.09 (m, 3H), 3.55 (m, 5H), 4.30-4.53 (m, 2H), 6.88 (d, 1H), 7.86 (d, 1H), 8.61 (s, 1H), 9.06 (s, 1H), 13.05 (s, 1H)

Workup

  1. customsynthesized by hydrogenation analogous to the one

Sources & evidence

ORD record
ord-761a450d04d54d62ae7e09c454999c80
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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