Trifluoroacetic acid → HCID 178457351, compound

HRID 2225216Notes

Reaction equation

HRID 2225216 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([N:14]([CH:16]([CH3:18])[CH3:17])[CH3:15])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:16]([N:14]([CH3:15])[C@H:11]1[CH2:12][CH2:13][C@@H:8]([NH2:7])[CH2:9][CH2:10]1)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178457354HCID 178457354, compound

Product 1

HCID 178457351HCID 178457351, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [cis-4-(isopropyl-methyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester (0.16 g, 0.6 mmol) in CH2Cl2 (3 mL) was cooled to 0° C., charged with trifluoroacetic acid (1 mL), and stirred at RT for 1 h before being concentrated in vacuo. The residue was dissolved in CH2Cl2 and concentrated in vacuo; this was repeated to afford N-isopropyl-N-methyl-cis-cyclohexane-1,4-diamine. A portion (25 mg, 0.15 mmol) of this material was dissolved in DMF (1 mL). The resulting solution was charged with N,N-diethylisopropylamine (0.13 mL, 0.7 mmol), {2-[2-(3-isopropyl-ureido)-5-trifluoromethyl-benzoylamino]-acetic acid (56 mg, 0.16 mmol), and BOP (97 mg, 0.22 mmol) and stirred for 14 h at RT. The reaction was partitioned between water and EtOAc, and organic phase was washed successively with sat. NH4Cl, water, and brine before being dried (Na2SO4), filtered, and concentrated in vacuo. Purification of the residue by reverse phase HPLC afforded the TFA salt of the title compound as a white powder after lyopholization. MS found: (M+H)+=500.3.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e4a35cfda134ff9aa1b02a2ba21895f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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