Hydrochloric Acid → HCID 86647623, compound

HRID 1186607Notes

Reaction equation

HRID 1186607 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:20]=[CH:19][C:11]([C:12]([O:14]C(C)(C)C)=[O:13])=[C:10]([N:21]([CH:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH2:4][CH2:3]1.[ClH:35].O1CCOCC1>ClCCl>[ClH:35].[ClH:35].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:20]=[CH:19][C:11]([C:12]([OH:14])=[O:13])=[C:10]([N:21]([CH:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)[C:22](=[O:27])[C:23]([F:25])([F:24])[F:26])[CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 86647622HCID 86647622, compound

Product 1

HCID 86647623HCID 86647623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-methylpiperazin-1-yl)-2-[(1-methylpiperidin-4-yl)(trifluoroacetyl)amino]benzoate (1.18 g, 2.435 mmol) was dissolved in dry dichloromethane (3 mL) under nitrogen atmosphere. A 4 M solution of HCl in dioxane (9.1 mL, 36.4 mmol, 15 eq) was then added dropwise and the mixture was stirred for 1.5 hours. A sticky solid was formed. 5 more equivalents of HCl were added and the mixture was stirred for 2 more hours. The solid was filtered, washed with DCM (10 mL) and diethyl ether (10 mL) and dried under vacuum at 60° C. for 2 hours. 1.06 g of title compound were obtained as a beige powder (87% yield).

Workup

  1. customA sticky solid was formed
  2. stirringthe mixture was stirred for 2 more hours
  3. filtrationThe solid was filtered
  4. washwashed with DCM (10 mL) and diethyl ether (10 mL)
  5. customdried under vacuum at 60° C. for 2 hours

Sources & evidence

ORD record
ord-9e192cd1d4f54e0ba93fa2bbb0a4aaf9
Source dataset
uspto-grants-2014_03
Patent number
US08673893B2

Reaction notes

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