Einecs 211-027-4 → HCID 10183180, compound

HRID 990802Notes

Reaction equation

HRID 990802 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]3[S:15][CH:16]=[C:17]([C:18]4[NH:22][N:21]=[C:20]([NH:23][C:24]5[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][CH:25]=5)[CH:19]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[Cl-].[NH+]1C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]3[S:15][CH:16]=[C:17]([C:18]4[NH:22][N:21]=[C:20]([NH:23][C:24]5[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][CH:25]=5)[CH:19]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 69401Einecs 211-027-4HCID 10205834HCID 10205834, compound

Product 1

HCID 10183180HCID 10183180, compoundYield 68.9%

Conditions

Temperature
180 °C

Procedure

4-{5-[7-(3-Methoxy-phenyl)-benzo[b]thiophen-3-yl]-1H-pyrazol-3-ylamino]-benzenesulfonamide (130 mg, 0.27 mmol) and pyridinium chloride (1.3 g) were combined in a sealed tube and heated at 180° C. for 2 h. The reaction was cooled, quenched with saturated NaHCO3 solution until the solid clump was broken up, and extracted with EtOAc (60 mL). Organics were washed with brine (25 mL), dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography gave 86 mg (68%) of 4-{5-[7-(3-hydroxy-phenyl)-benzo[b]thiophen-3-yl]-1H-pyrazol-3-ylamino]-benzenesulfonamide as a white solid. 1H NMR (300 MHz, DMSO-d6) δ12.67 (s, 1H), 9.72 (s, 1H), 9.13 (s, 1H), 8.04 (s, 1H), 8.01 (s, 1H), 7.58-7.67 (m, 3H), 7.45-7.51 (m, 3H), 7.36 (t, 1H, J=7.8 Hz), 7.06-7.14 (m, 4H), 6.87 (d, 1H, J=7.5 Hz), 6.33 (s, 1H). Anal. (C23H18N4O3S2.0.1 H2O) C, H, N, S. Calculated C=59.49; H=3.95; N=12.07; S=13.81; found C=59.51; H=3.95; N=12.20; S=13.63.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with saturated NaHCO3 solution until the solid clump
  3. extractionextracted with EtOAc (60 mL)
  4. washOrganics were washed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-d02057f7ba1c4c2794b523d837606ee1
Source dataset
uspto-grants-2002_10
Patent number
US06462069B2

Reaction notes

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