Trifluoroacetic acid → HCID 70874367, compound

HRID 2208714Notes

Reaction equation

HRID 2208714 reaction equation
[CH:1]1([N:6]([CH3:40])[C:7]2[CH:8]=[C:9]([C:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH:28]=3)[CH:10]=[C:11]([C:14](=[O:26])[NH:15][CH2:16][C:17]3[C:18](=[O:25])[NH:19][C:20]([CH3:24])=[CH:21][C:22]=3[CH3:23])[C:12]=2[CH3:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([N:6]([CH3:40])[C:7]2[C:12]([CH3:13])=[C:11]([CH:10]=[C:9]([C:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH:28]=3)[CH:8]=2)[C:14]([NH:15][CH2:16][C:17]2[C:18](=[O:25])[NH:19][C:20]([CH3:24])=[CH:21][C:22]=2[CH3:23])=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86719539HCID 86719539, compound

Product 1

HCID 70874367HCID 70874367, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(3-(cyclopentyl(methyl)amino)-5-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (0.800 g, 1.45 mmol) in DCM was added TFA (3 mL) and the reaction mixture was stirred at RT for 2 h. On completion, reaction was concentrated to dryness. Residue was basified with aqueous sodium bicarbonate till pH 8 and aqueous layer extracted with 20% MeOH/DCM. Combined organic layers were dried over sodium sulfate and concentrated to afford crude material which was purified by preparative HPLC to afford the desired compound (0.620 g, 95%).

Workup

  1. customOn completion, reaction
  2. concentrationwas concentrated to dryness
  3. extractionextracted with 20% MeOH/DCM
  4. dry with materialCombined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford crude material which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f30f99afd5624b48a2ecb1275bcd8932
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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