Acetonitrile → HCID 86687618, compound

HRID 1473558Notes

Reaction equation

HRID 1473558 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([O:21]C4C(F)=C(F)C(F)=C(F)C=4F)(=[O:20])=O)=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)[CH:7]=1.[S:35]1[C:39]([NH2:40])=[N:38][CH:37]=[N:36]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:40][C:39]4[S:35][N:36]=[CH:37][N:38]=4)(=[O:20])=[O:21])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 2902745-Amino-1,2,4-thiadiazoleHCID 86687617HCID 86687617, compound

Product 1

HCID 86687618HCID 86687618, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A round-bottom flask was charged with perfluorophenyl 1-(5-chloro-2-methoxyphenyl)isoquinoline-6-sulfonate (INTERMEDIATE XXXX, 150.33 mg, 0.291 mmol), 1,2,4-thiadiazol-5-amine (35.4 mg, 0.350 mmol), and cesium carbonate (285 mg, 0.874 mmol). acetonitrile (1457 μl) was added, and the mixture was stirred for 1.5 h. The mixture was diluted with EtOAc and 0.5 N aq. HCl. The layers were separated, and the organic extract was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was concentrated from MeOH. The residue was taken up in MeOH, sonicated, and filtered on a membrane filter. The collected solid was washed with MeOH (3×), dried under a stream of N2 (g), then dried under vacuum to give 1-(5-chloro-2-methoxyphenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (100.0 mg, 0.231 mmol, 79% yield) as a cream-colored solid. 1H NMR (400 MHz, DMSO-d6) δ=8.69 (d, J=5.7 Hz, 1H), 8.58 (d, J=1.7 Hz, 1H), 8.49 (s, 1H), 8.15 (d, J=5.5 Hz, 1H), 7.89 (dd, J=1.9, 8.9 Hz, 1H), 7.75 (d, J=8.9 Hz, 1H), 7.59 (dd, J=2.7, 8.9 Hz, 1H), 7.40 (d, J=2.7 Hz, 1H), 7.26 (d, J=9.0 Hz, 1H), 3.65 (s, 3H). m/z (ESI) 432.9 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe organic extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe residue was concentrated from MeOH
  8. customsonicated
  9. filtrationfiltered on a membrane
  10. filtrationfilter
  11. washThe collected solid was washed with MeOH (3×)
  12. dry with materialdried under a stream of N2 (g)
  13. customdried under vacuum

Sources & evidence

ORD record
ord-8ea2df3754df4b3f92e54246ef6e128b
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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