Trifluoroacetic acid → HCID 178432178, compound

HRID 1467174Notes

Reaction equation

HRID 1467174 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C:14]([NH:17][C:18](=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)([CH3:16])[CH3:15])[N:5]=[C:4]([CH3:33])[C:3]=1[C:34]([OH:36])=[O:35].[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl>[F:37][C:38]([F:43])([F:42])[C:39]([O-:41])=[O:40].[NH3+:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]([NH:17][C:14]([CH3:16])([CH3:15])[CH2:13][O:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([NH3+:1])=[C:3]([C:34]([OH:36])=[O:35])[C:4]([CH3:33])=[N:5]2)=[O:32].[F:37][C:38]([F:43])([F:42])[C:39]([O-:41])=[O:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66746395HCID 66746395, compound

Product 1

HCID 178432178HCID 178432178, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-amino-5-(2-(6-(tert-butoxycarbonylamino)hexanamido)-2-methylpropoxy)-2-methylquinoline-3-carboxylic acid (Example 152a) (59.6 mg, 0.12 mmol) in CH2Cl2 (9.0 mL) was treated with trifluoroacetic acid (1.0 mL) at room temperature. After being stirred at room temperature for 2 h the reaction mixture was evaporated to dryness. The residue was dissolved in H2O (5.0 mL) and the product was isolated by preparative HPLC (RPC18, H2O→CH3CN gradient). The appropriate fractions were collected and evaporated under reduced pressure. The residue was dried in a dessicator over phosphorus pentoxide to give 43.6 mg (58%) of 5-(2-(6-ammoniohexanamido)-2-methylpropoxy)-3-carboxy-2-methylquinolin-4-aminium trifluoroacetate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.56 (s, 1H), 9.98 (s, 1H), 9.40 (s, 1H), 7.88 (t, J=8.3 Hz, 1H), 7.75 (s, 1H), 7.72-7.56 (m, 3H), 7.42 (d, J=7.9 Hz, 1H), 7.25 (d, J=8.1 Hz, 1H), 4.42 (s, 2H), 2.81 (s, 3H), 2.72-2.60 (m, 2H), 2.08 (t, J=7.3 Hz, 2H), 1.50-1.39 (m, 4H), 1.38 (s, 6H), 1.26-1.14 (m, 2H). MS 404 (M+).

Workup

  1. customwas evaporated to dryness
  2. dissolutionThe residue was dissolved in H2O (5.0 mL)
  3. customthe product was isolated by preparative HPLC (RPC18, H2O→CH3CN gradient)
  4. customThe appropriate fractions were collected
  5. customevaporated under reduced pressure
  6. dry with materialThe residue was dried in a dessicator over phosphorus pentoxide

Sources & evidence

ORD record
ord-382bf39eeafb41fc8d2e0c028a2cfa61
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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