Trifluoroacetic acid → HCID 44217941, compound

HRID 1928740Notes

Reaction equation

HRID 1928740 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([NH:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[C:23]([NH:28][C@H:29]2[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:31][CH2:30]2)[CH:22]=[CH:21]3)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O>[C@H:29]1([NH:28][C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[CH:26][CH:27]=[C:18]([NH:17][C:15]([NH:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[O:16])[CH:19]=3)[N:24]=2)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 68631824HCID 68631824, compound

Product 1

HCID 44217941HCID 44217941, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-{3-[2-((R)-Indan-1-ylamino)-quinolin-6-yl]-ureido}-piperidine-1-carboxylic acid tert-butyl ester (20 mg, 0.040 mmol) was dissolved in methylene chloride (1.0 mL). At 0° C. trifluoroacetic acid (0.030 mL, 0.40 mmol) was added and the reaction mixture was stirred at ambient temperature over night. 20% sodium carbonate solution in water was added and the mixture was extracted with ethyl acetate (3×10 mL). The combined organic phases were dried on magnesium sulfate, filtered and evaporated. The residue was subjected to column chromatography (silica gel, methylene chloride:methanol gradient=95:5→2:1) to yield the title compound (5.0 mg; 31%) as an off-white solid; MS: m/e=402.5 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  2. customThe combined organic phases were dried on magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d718441e824e45e186825a66ac91ed69
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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