Hydrochloric Acid → HCID 178432514, compound

HRID 1812373Notes

Reaction equation

HRID 1812373 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])=[CH:6][C:5]([NH:15][C:16]2[C:21]([C:22]3[N:30]=[C:29]([CH3:31])[N:28]=[C:27]4[C:23]=3[N:24]=[CH:25][N:26]4C3CCCCO3)=[CH:20][C:19]([CH:38]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH3:39])=[CH:18][N:17]=2)=[CH:4][N:3]=1.Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[OH-].[Na+]>[OH-].[Na+].C1COCC1>[Cl:1][C:2]1[C:7]([NH:8][S:9]([N:12]([CH3:14])[CH3:13])(=[O:10])=[O:11])=[CH:6][C:5]([NH:15][C:16]2[C:21]([C:22]3[N:30]=[C:29]([CH3:31])[N:28]=[C:27]4[C:23]=3[N:24]=[CH:25][NH:26]4)=[CH:20][C:19]([CH:38]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH3:39])=[CH:18][N:17]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23674961citric acid NaOHHCID 86647080N'-(2-chloro-5-((3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)-5-(1-(4-morpholinyl)ethyl)-2-pyridinyl)amino)-3-pyridinyl)-N,N-dimethylsulfamide

Product 1

HCID 178432514HCID 178432514, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 20 mL scintillation vial, N′-(2-chloro-5-((3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)-5-(1-(4-morpholinyl)ethyl)-2-pyridinyl)amino)-3-pyridinyl)-N,N-dimethylsulfamide (0.047 g, 0.072 mmol) and 5 N hydrochloric acid (0.5 mL, 2.5 mmol) were mixed into THF (2 mL). The solution was stirred at room temperature for 30 min. Buffer (pH 5, citric acid/NaOH) (10 mL) was added and the pH was further adjusted to about 5 using a few drops of 6 N NaOH. The aqueous phase was extracted with 10% isopropanol in chloroform (2×20 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to afford N′-(2-chloro-5-((3-(2-methyl-9H-purin-6-yl)-5-(1-(4-morpholinyl)ethyl)-2-pyridinyl)amino)-3-pyridinyl)-N,N-dimethylsulfamide (0.0237 g, 58% yield) as a yellow powder. 1H NMR (400 MHz, chloroFORM-d) δ ppm 13.10 (s, 1H) 11.17 (br. s., 1H) 9.81 (br. s., 1H) 8.86 (d, J=2.15 Hz, 1H) 8.51 (d, J=2.35 Hz, 1H) 8.34 (d, J=1.37 Hz, 1H) 8.22 (s, 1H) 6.81 (br. s., 1H) 3.74 (br. s., 4H) 3.56 (d, J=6.65 Hz, 1H) 2.96 (s, 9H) 2.44-2.66 (m, 4H) 1.50 (d, J=6.65 Hz, 3H). m/z (ESI, positive ion): 573.0 (M+H)+.

Workup

  1. extractionThe aqueous phase was extracted with 10% isopropanol in chloroform (2×20 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8935e7a7734b43f3b8f72bf95fba783c
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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