Hydrochloric Acid → 6-Chloro-16-thia-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene 16,16-dioxide

HRID 541810Notes

Reaction equation

HRID 541810 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=3)[CH:14]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl>COCCO.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[Cl:26][C:25]1[CH:24]=[N:23][C:22]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH:3]=3)[S:8](=[O:10])(=[O:9])[NH:11][CH2:12][C:13]3[CH:14]=[C:15]([NH:19][C:20]=1[N:21]=2)[CH:16]=[CH:17][CH:18]=3

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 579626943-Amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamide

Product 1

HCID 579622376-Chloro-16-thia-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene 16,16-dioxide

Reagents, catalysts & solvents 3

HCID 80192-MethoxyethanolSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamide (38.0 mg, 0.089 mmol) in 2-methoxyethanol (0.49 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (45 μL). The resulting mixture was heated at 150° C. in the microwave for 15 min. The mixture was diluted with Na2CO3 (aq), extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the crude, which was purified by Combi-Flash column chromatography (4 g column, 0 to 50% EtOAc in Hex) to the desired product as a white powder (7 mg, 20%). LCMS for C17H14ClN5O2S (M+H)+: m/z=388.0, 390.0. 1H NMR (400 MHz, CD3OD): δ 7.62 (m, 1H), 7.54 (s, 1H), 7.28 (t, J=2.0 Hz, 1H), 7.08 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 6.78 (t, J=8.0 Hz, 1H), 6.35 (m, 1H), 6.18 (ddd, J=8.0, 1.6, 1.0 Hz, 1H), 5.98 (m, 1H), 5.82 (ddd, J=7.6, 2.0, 1.0, 1H), 4.20 (s, 2H).

Workup

  1. extractionextracted with EtOAc three times
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude, which
  6. customwas purified by Combi-Flash column chromatography (4 g column, 0 to 50% EtOAc in Hex) to the desired product as a white powder (7 mg, 20%)

Sources & evidence

ORD record
ord-d09e1aa625fa4b868ea34a783a8c668f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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