5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid → HCID 46932809, compound

HRID 1192104Notes

Reaction equation

HRID 1192104 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[NH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]1>>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:21][CH:22]2[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]2)=[O:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acidHCID 178511715HCID 178511715, compound

Product 1

HCID 46932809HCID 46932809, compound

Procedure

Prepared according to the procedure described for example 70 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (150 mg, 0.43 mmol) and trans-4-aminocyclohexanol (59 mg, 0.51 mmol). The title compound was obtained as a solid (45 mg, 23% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, m), 8.58 (1H, m), 8.47 (1H, s), 4.56 (1H, d), 3.55 (1H, m), 3.37 (1H, m), 1.78 (4H, m), 1.20 (6H, m). MS m/z: 446.19, 448.18 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-48c9cce061404982b8199ce6a3eb4aa9
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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