N,N-Dimethylpiperidin-4-amine → HCID 67494580, compound

HRID 1192229Notes

Reaction equation

HRID 1192229 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH:19]=O)=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22].[CH3:25][N:26]([CH3:33])[CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:30]2[CH2:31][CH2:32][CH:27]([N:26]([CH3:33])[CH3:25])[CH2:28][CH2:29]2)=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

3

Reactant 2

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 60207450HCID 60207450, compound

Product 1

HCID 67494580HCID 67494580, compound

Procedure

Prepared according to the procedure described for step D of example 223 from 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-oxopropyl)thiophene-2-carboxamide (100 mg, 0.23 mmol) and N,N-dimethylpiperidin-4-amine (6.0 mg, 0.28 mmol). The title compound was afforded as a solid (30.0 mg, 25% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.02 (2H, s), 8.88 (1H, m), 8.46 (1H, s), 3.23 (2H, m), 2.93 (2H, m), 2.31 (9H, m), 1.91 (2H, m), 1.79 (2H, m), 1.66 (2H, m), 1.41 (2H, m). MS m/z: 518.16, 520.15 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-97a5cefd00724145bf64da8a87bfb16a
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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