Hydrochloric Acid → HCID 178440279, compound

HRID 411591Notes

Reaction equation

HRID 411591 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[C:10]=1[N:17]1[C:21]2=[N:22][C:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=3)=[N:24][C:25](=[O:26])[C:20]2=[C:19]([CH:35]([CH3:37])[CH3:36])[NH:18]1.CCN(CC)CC.Cl.[CH3:46][C:47]([OH:50])([CH3:49])[CH3:48]>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[C:10]=1[N:17]1[C:21]2=[N:22][C:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([NH:34][S:2]([NH:5][C:6]([O:50][C:47]([CH3:49])([CH3:48])[CH3:46])=[O:7])(=[O:4])=[O:3])=[CH:30][CH:29]=3)=[N:24][C:25](=[O:26])[C:20]2=[C:19]([CH:35]([CH3:37])[CH3:36])[NH:18]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 178440271HCID 178440271, compound

Product 1

HCID 178440279HCID 178440279, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, cooled solution of 0.11 mL (1.26 mmol) of chlorosulfonyl isocyanate in 5 mL of CH2Cl2 was added 0.13 mL of t-BuOH. The solution was stirred 10 min. and added to a stirred, cooled (0° C.) solution of 231 mg (0.5 mmol) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-aminobenzyl)pyrazolo[3,4-d]pyrimidin-4-one and 0.2 mL (1.4 mmol) of Et3N in 5 mL of CH2C1-2. The solution was stirred 1 h warming to ambient temperature, and it was then poured into 1 N aq. HCl. The mixture was extracted with EtOAc, and the organic extract was washed (brine), dried (MgSO4), concentrated under reduced pressure, and chromatographed on silica gel (elution with 1:1 EtOAc-hexanes, then EtOAc) to afford 250 mg (78%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(t-butoxycarbonylaminosulfonamido)benzyl)pyrazolo[3,4-d]pyrimidin-4-one as a white solid. 1H NMR (300 MHz, DMSO) δ 12.44(s, 1H); 11.12(br. s, 1H); 9.70(br. s, 1H); 7.97(s, 2H); 7.21(d, 2H, J=8.4 Hz); 7.02(d, 2H, J=8.4 Hz); 3.78(s, 2H); 3.19-3.30(m, 1H); 1.27(d, 6H, J=6.9 Hz); 1.21(s, 9H).

Workup

  1. additionadded to a stirred
  2. stirringThe solution was stirred 1 h
  3. extractionThe mixture was extracted with EtOAc
  4. extractionthe organic extract
  5. washwas washed (brine)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customchromatographed on silica gel (
  9. washelution with 1:1 EtOAc-hexanes

Sources & evidence

ORD record
ord-f257ec0c065849b382c7d871caa297bb
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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