(R)-piperidin-3-yl(pyrrolidin-1-yl)methanone → (R)-(1-(6-Amino-4-methyl-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 931250Notes

Reaction equation

HRID 931250 reaction equation
Cl.Cl.NC1C(N)=CN=C([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)N=1.Cl[C:25]1[N:30]=[C:29]([NH2:31])[C:28]([N+:32]([O-:34])=[O:33])=[C:27]([CH3:35])[CH:26]=1.N1CCC[C@@H](C(N2CCCC2)=O)C1>>[NH2:31][C:29]1[N:30]=[C:25]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[O:18])[CH2:12]2)[CH:26]=[C:27]([CH3:35])[C:28]=1[N+:32]([O-:34])=[O:33]

Participants

4

Reactant 3

HCID 7169819(R)-piperidin-3-yl(pyrrolidin-1-yl)methanoneHCID 707010046-Chloro-4-methyl-3-nitropyridin-2-amineHCID 89853293(R)-(1(4,5-Diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

Product 1

HCID 117966447(R)-(1-(6-Amino-4-methyl-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Procedure

(R)-(1-(6-Amino-4-methyl-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone was prepared using a method analogous to the one used for Intermediate 2, Step 1 but using 6-chloro-4-methyl-3-nitropyridin-2-amine and (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone as starting materials. The reaction mixture was run at 70° C. for 1 h. MS (ES+APCI) (M+H) 333.9; LCMS retention time 4.322 min (Method Z).

Sources & evidence

ORD record
ord-13f347a250e74f2bb4d792018465fcbd
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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