Hydrochloric Acid → HCID 178432514, compound

HRID 1621965Notes

Reaction equation

HRID 1621965 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 5N 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 6N 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-b4619e0b48ac46bda3c310af48828356
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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