Trifluoroacetic acid → HCID 117843259, compound

HRID 2209191Notes

Reaction equation

HRID 2209191 reaction equation
[C:1](O)([C:3](F)(F)F)=[O:2].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[C:24]([O:31][C@@H:32]([C@H:34]3[CH2:38][NH:37][C:36](=[O:39])[CH2:35]3)[CH3:33])[C:25]3[S:29][CH:28]=[N:27][C:26]=3[CH:30]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CCN(CC)CC.C(OC(=O)C)(=O)C>C(Cl)Cl>[C:1]([N:19]1[CH2:18][CH2:17][N:16]([C:15]2[CH:14]=[CH:13][C:12]([C:22]3[CH:23]=[C:24]([O:31][C@@H:32]([C@H:34]4[CH2:38][NH:37][C:36](=[O:39])[CH2:35]4)[CH3:33])[C:25]4[S:29][CH:28]=[N:27][C:26]=4[CH:30]=3)=[CH:11][C:10]=2[O:9][CH3:8])[CH2:21][CH2:20]1)(=[O:2])[CH3:3]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117843306HCID 117843306, compound

Product 1

HCID 117843259HCID 117843259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude TFA salt of 4.34 (0.072 mmol) was suspended in DCM (1 mL) and Et3N (72 μL, 0.51 mmol) was added followed by acetic anhydride (8.2 μL, 0.086 mmol). The resulting mixture was stirred 1.5 h and was partitioned between EtOAc, water, and brine. The phases were separated, and the aqueous phase was extracted with EtOAc. The combined organic phase was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography (0-15% MeOH in DCM) to afford (R)-4-((R)-1-((5-(4-(4-acetylpiperazin-1-yl)-3-methoxyphenyl)benzo[d]thiazol-7-yl)oxy)ethyl)pyrrolidin-2-one (4.35).

Workup

  1. customwas partitioned between EtOAc, water, and brine
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (0-15% MeOH in DCM)

Sources & evidence

ORD record
ord-8c9c450429b04262850a38bfecb2df82
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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