Trifluoroacetic acid → HCID 178463297, compound

HRID 1469161Notes

Reaction equation

HRID 1469161 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([C:18]2[CH:23]=[C:22]([C:24]#[C:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:21]=[C:20]([C:33](=[O:45])[NH:34][CH2:35][C:36]3[C:37](=[O:44])[NH:38][C:39]([CH3:43])=[CH:40][C:41]=3[CH3:42])[C:19]=2[CH3:46])[CH2:16][CH3:17])[CH2:11][CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:42][C:41]1[CH:40]=[C:39]([CH3:43])[NH:38][C:37](=[O:44])[C:36]=1[CH2:35][NH:34][C:33](=[O:45])[C:20]1[CH:21]=[C:22]([C:24]#[C:25][CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:23]=[C:18]([N:15]([CH2:16][CH3:17])[C@H:12]2[CH2:13][CH2:14][C@H:9]([NH:7][CH3:6])[CH2:10][CH2:11]2)[C:19]=1[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178463298HCID 178463298, compound

Product 1

HCID 178463297HCID 178463297, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl((trans)-4-((3-(((4,6-dimethyl-2-oxo-1,2-dihydro pyridin-3-yl)methyl)carbamoyl)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)phenyl)(ethyl)amino)cyclohexyl)(methyl)carbamate (1 equiv.) in DCM at 0° C., TFA (3 equiv.) was added and reaction was stirred for 2 h at room temperature. After completion, reaction was concentrated to dryness. The residue was then basified with Na2CO3 (aq.) to pH 8 and the aqueous layer was extracted with 20% methanol in DCM. The combined organic layers were dried over Na2SO4 and solvent was removed under reduced pressure to afford the title compound (99% yield) which was used in the next reaction without further purification.

Workup

  1. customreaction
  2. customAfter completion, reaction
  3. concentrationwas concentrated to dryness
  4. extractionthe aqueous layer was extracted with 20% methanol in DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4 and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-af4fbf18603744689a860cef02efe685
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

Loading…