Hydrochloric Acid → HCID 67147940, compound

HRID 490528Notes

Reaction equation

HRID 490528 reaction equation
Cl.C(OC(=O)[NH:8][CH:9]1[CH2:12][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][C:21]([C:23]4[C:31]5[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=5)[N:25]([CH3:36])[CH:24]=4)=[CH:22][C:15]=23)[CH2:10]1)(C)(C)C.[OH-].[Na+]>CO.ClCCl.O>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]([CH3:36])[CH:24]=[C:23]2[C:21]1[NH:20][C:16]2=[N:17][CH:18]=[CH:19][C:14]([CH2:13][N:11]3[CH2:12][CH:9]([NH2:8])[CH2:10]3)=[C:15]2[CH:22]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67147746HCID 67147746, compound

Product 1

HCID 67147940HCID 67147940, compoundYield 19.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.27 cm3 of hydrochloric acid (4N in dioxane) is added to a solution of 0.051 g of {1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-yl}carbamic acid tert-butyl ester in 3 cm3 of methanol and 0.5 cm3 of dichloromethane, at a temperature in the region of 20° C. The reaction medium is stirred at room temperature for 24 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 4 cm3 of water and is then neutralized with 1N sodium hydroxide to pH 10. 12 cm3 of dichloromethane are added. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.008 g of 1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-ylamine is obtained, the characteristics of which are as follows:

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. customThe residue obtained
  3. customAfter separation of the phases
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-419692ad12e04ca5b8cb3c596ade6aeb
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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