Acetic Acid → HCID 60207451, compound

HRID 1192228Notes

Reaction equation

HRID 1192228 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].[OH:25][CH:26]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1.C(O)(=O)C.[Na]>O1CCCC1.O>[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:28]2[CH2:29][CH2:30][CH2:31][CH:26]([OH:25])[CH2:27]2)=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 232933-HydroxypiperidineHCID 5360545SodiumHCID 60207450HCID 60207450, compound

Product 1

HCID 60207451HCID 60207451, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-oxopropyl)thiophene-2-carboxamide (0.13 g, 0.32 mmol) and 3-hydroxy-piperidine (89.0 mg, 0.38 mmol) in tetrahydrofuran (3.0 mL) under nitrogen, was added acetic acid (0.2 mL). The resulting mixture was stirred at ambient temperature for 30 minutes. Then sodium triacetoxyboronhydride was added and the reaction mixture was stirred at ambient temperature for additional 4 hours. After this time, the reaction mixture was diluted with water and extracted with ethylacetate. The organic layer was separated, dried (Na2SO4) and concentrated. The crude residue was purified by silica gel chromatography using a 90:10 mixture of dichloromethane and methanol as eluent to afford the title product as a solid (14.0 mg, 37% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.99 (2H, m), 8.83 (1H, m), 8.41 (1H, s), 4.58 (1H, m), 3.19 (2H, m), 2.80 (1H, m), 2.61 (1H, m), 2.27 (2H, m), 1.76 (2H, m), 1.61 (3H, m), 1.38 (1H, m), 1.23 (1H, m), 1.06 (1H, m). MS m/z: 491.11, 493.13 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for additional 4 hours
  2. extractionextracted with ethylacetate
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography
  7. additiona 90:10 mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-cce52c6a4cc7475490f27081155105df
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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