Hydrochloric Acid → HCID 86694539, compound

HRID 1406568Notes

Reaction equation

HRID 1406568 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:15]1[C:24]2[C:19](=[C:20]([N:25]3[C:29]([NH2:30])=[C:28]4[CH2:31][CH2:32][CH2:33][C:27]4=[N:26]3)[CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][N:16]=1.Cl>N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:30][C:29]2[N:25]([C:20]3[CH:21]=[CH:22][CH:23]=[C:24]4[C:19]=3[CH:18]=[CH:17][N:16]=[CH:15]4)[N:26]=[C:27]3[CH2:33][CH2:32][CH2:31][C:28]=23)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 86694540HCID 86694540, compound

Product 1

HCID 86694539HCID 86694539, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-t-butylbenzenesulfonyl chloride (0.075 g, 0.32 mmol) and 2-(isoquinolin-5-yl)-2,4,5,6-tetrahydrocyclopentapyrazol-3-amine (0.050 g, 0.20 mmol) in pyridine (1 mL) was stirred at room temperature for 1 h. The reaction mixture was added 1 N aqueous hydrochloric acid and extracted with in 2:1 CH2Cl2/iPrOH (2×10 mL). The combine organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The resulting material was purified by reverse phase HPLC(C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the title compound as a white solid (0.025 g, 0.056 mmol, 28%). 1H NMR (400 MHz, DMSO-d6) δ 10.10 (s, 1H), 9.35 (s, 1H), 8.42 (d, J=6.0 Hz, 1H), 8.17 (d, J=8.8 Hz, 1H), 7.68 (t, J=8.0 Hz, 1H), 7.49 (d, J=7.2 Hz, 1H), 7.41-7.37 (m, 3H), 7.18 (d, J=4.8 Hz, 1H), 2.64 (t, J=7.2 Hz, 2H), 2.21 (pent, J=7.2 Hz, 2H), 2.06 (t, J=7.5 Hz, 2H), 1.25 (s, 9H); MS: (ES) m/z calculated for C25H27N4O2S [M+H]+ 447.2. found 447.1.

Workup

  1. extractionextracted with in 2:1 CH2Cl2/iPrOH (2×10 mL)
  2. dry with materialThe combine organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting material was purified by reverse phase HPLC(C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-c9ac2fc969004c01a202de82f7ef7102
Source dataset
uspto-grants-2014_12
Patent number
US08916601B2

Reaction notes

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