Hydrochloric Acid → HCID 24826144, compound

HRID 910935Notes

Reaction equation

HRID 910935 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([S:14][C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([OH:20])=O)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.C(N(CC)CC)C.C([Cl:36])(=O)OCC.[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][NH2:41].[ClH:43]>C(Cl)Cl.C1COCC1>[ClH:36].[ClH:43].[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][NH:41][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([S:14][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[CH:13]=2)[CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66053N,N-DimethylethylenediamineHCID 24826068HCID 24826068, compound

Product 1

HCID 24826144HCID 24826144, compoundYield 42.36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A 100 mL round-bottomed flask was charged with 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)benzoic acid (0.100 g, 0.2912 mmol) and THF (30 mL) and cooled to −5° C. Triethylamine (0.08840 g, 0.8736 mmol) and ethyl carbonochloridate (0.02784 mL, 0.2912 mmol) were added successively. The reaction mixture was stirred at −5° C. for 30 minutes. N1,N1-dimethylethane-1,2-diamine (0.07701 g, 0.8736 mmol) was added and stirred at −5° C. for 30 minutes and room temperature for 1 hour. An aqueous workup was done, the organic layer was dried and concentrated, and the residue was purified by silica gel chromatography to give the free base. The free base was dissolved in DCM, and 2M HCl was added. The solution was concentrated to provide N-(2-(dimethylamino)ethyl)-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)benzamide dihydrochloride (0.060 g, 42.36% yield). 1H NMR (d6-DMSO) δ 11.34 (bs, 1H), 9.97 (bs, 1H), 8.94 (t, 1H), 8.13 (m, 2H), 8.07 (d, 1H), 7.79 (d, 1H), 7.67 (t, 1H), 6.80 (s, 1H), 6.66 (s, 1H), 6.58 (s, 1H), 3.63 (m, 2H), 2.26 (m, 2H), 2.82 (d, 6H), 2.21 (s, 3H); Mass spectrum (apci) m/z=414.0 (M+H-2HCl).

Workup

  1. stirringstirred at −5° C. for 30 minutes and room temperature for 1 hour
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was purified by silica gel chromatography
  5. customto give the free base
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-81e86e19646846a998925e6cef99152e
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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