Ethyl 4-cyclopropylpyrimidine-2-carbimidate → HCID 178521023, compound

HRID 931238Notes

Reaction equation

HRID 931238 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=[CH:30][C:31]([N:35]2[CH2:40][CH2:39][CH2:38][C@@H:37]([C:41](N3CCCC3)=O)[CH2:36]2)=[N:32]C=1N.NC1N=C(N2CCC[C@@H](C(N3CCOCC3)=O)C2)C=CC=1[N+]([O-])=O.C1(C2C=CN=C(C(=N)OCC)N=2)CC1>>[CH:37]1([C:38]2[CH:39]=[CH:40][N:35]=[C:31]([C:30]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)[N:32]=2)[CH2:36][CH2:41]1

Participants

5

Reactant 4

HCID 89853794Ethyl 4-cyclopropylpyrimidine-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 178521023HCID 178521023, 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 42. MS (ES+APCI) (M+H) 434.2; LCMS retention time 1.996 min (Method G).

Workup

  1. customsynthesized by hydrogenation analogous to the one

Sources & evidence

ORD record
ord-8130070eb213406ab6afc8a2e507cf95
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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