Hydrochloric Acid → HCID 11404068, compound

HRID 2054892Notes

Reaction equation

HRID 2054892 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([F:27])[C:17]3[C:21]([NH2:22])=[C:20]([C:23](=[O:25])[NH2:24])[S:19][C:18]=3[CH:26]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[NH2:22][C:21]1[C:17]2[C:16]([F:27])=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]3)=[CH:26][C:18]=2[S:19][C:20]=1[C:23]([NH2:24])=[O:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59656691HCID 59656691, compound

Product 1

HCID 11404068HCID 11404068, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.055 g (0.14 mmol) of [1-(3-amino-2-carbamoyl-4-fluoro-benzo[b]thiophen-6-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester in CH2Cl2 (1 mL) was added 0.07 mL (0.3 mmol) of a 4.0 M solution of HCl in 1,4-dioxane. The mixture was stirred at room temperature for 3 days during which time a solid precipitated from solution. The solid was collected by filtration and washed with CH2Cl2. The material was purified by reverse phase HPLC to provide 0.010 g (18%) of the title compound as a white solid. MS calc. for C14H17FN4OS [M+H]+: 309.38. Found: 309.26.

Workup

  1. customprecipitated from solution
  2. filtrationThe solid was collected by filtration
  3. washwashed with CH2Cl2
  4. customThe material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c869e79feeb149ba9b40e45a501c633c
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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