6-Cyclopropylpicolinaldehyde → HCID 178484577, compound

HRID 931239Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:19]([O-])=O.[CH:22]1([C:25]2[N:30]=[C:29]([CH:31]=O)[CH:28]=[CH:27][CH:26]=2)[CH2:24][CH2:23]1>>[CH:22]1([C:25]2[N:30]=[C:29]([C:31]3[NH:1][C:2]4=[N:7][C:6]([N:8]5[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH2:9]5)=[CH:5][CH:4]=[C:3]4[N:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:24][CH2:23]1

Participants

Reactant 2

HCID 193617216-Cyclopropylpicolinaldehyde

HCID 117966493(R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide

Product 1

HCID 178484577HCID 178484577, compound

Procedure

The title compound was prepared using a method analogous to the one used for Example 112 but using (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide and 6-cyclopropylpicolinaldehyde as starting materials. 1H NMR (300 MHz, CDCl3) δ 1.01-1.18 (m, 4H), 1.63-1.74 (m, 1H), 1.84 (m, 1H), 1.93 (m, 2H), 2.10 (br s, 1H), 2.85 (br s, 1H), 2.96-3.03 (m, 3H), 3.08 (m, 1H), 3.15 (s, 3H), 3.50 (s, 1H), 4.35 (d, 1H), 4.50 (d, 1H), 6.73 (d, 1H), 7.20 (d, 1H), 7.68 (d, 1H), 7.89 (d, 1H), 8.10 (br s, 1H), 10.14 (br. s, 1H); MS (ES+APCI) (M+H) 391.2; LCMS retention time 1.831 min (Method W).

Sources & evidence

ORD record: ord-1668584955cc43ae97f38fd2aaa1249e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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