HCID 136353338, compound → HCID 136358073, compound

HRID 1034961Notes

Reaction equation

HRID 1034961 reaction equation
C(O[C:9](=O)[N:10](C)[CH2:11][C:12]1[C:24]2[C:23]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=3[C:17](=[O:25])[NH:16][C:15]=2[N:14]([CH3:26])[N:13]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.C(#N)C>[CH3:26][N:14]1[C:15]2[NH:16][C:17](=[O:25])[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=3[C:24]=2[C:12]([CH2:11][NH:10][CH3:9])=[N:13]1

Participants

4

Reactant 1

HCID 136353338HCID 136353338, compound

Product 1

HCID 136358073HCID 136358073, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 38A (160 mg) in trifluoroacetic acid (10 mL) was heated at 60° C. for 18 hours. The mixture was cooled, diluted with acetonitrile and concentrated. The residue was purified by HPLC (Zorbax C-8, 0.1% trifluoroacetic acid/acetonitrile/water) and the trifluoroacetate salt dissolved in methanol and treated with a solution of hydrochloric acid in ether to provide the title compound as the hydrochloride salt (82 mg, 79%). 1H NMR (DMSO-d6): 1.67-1.79 (m, 4H), 2.38-2.45 (m, 2H), 2.66 (t, J=4.3 Hz, 3H), 2.84-2.95 (m, 2H), 3.86 (s, 3H), 4.40-4.44 (m, 2H), 9.06 (br s, 1H), 12.17 (br s, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was purified by HPLC (Zorbax C-8, 0.1% trifluoroacetic acid/acetonitrile/water) and the trifluoroacetate salt
  4. dissolutiondissolved in methanol
  5. additiontreated with a solution of hydrochloric acid in ether

Sources & evidence

ORD record
ord-ff5289990d9c41b8b32da4771cfa5aa3
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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