Trifluoroacetic acid → HCID 67468650, compound

HRID 1476966Notes

Reaction equation

HRID 1476966 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[NH:12][C:11](=[O:16])[C:10]=1[CH2:17][NH:18][C:19]([C:21]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][C:33]([N:36]3[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][C@H:37]3[CH3:49])=[N:34][CH:35]=2)[CH:27]=[C:26]2[C:22]=1[C:23]([CH3:53])=[CH:24][N:25]2[CH:50]([CH3:52])[CH3:51])=[O:20]>C(Cl)Cl>[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[NH:12][C:11](=[O:16])[C:10]=1[CH2:17][NH:18][C:19]([C:21]1[C:22]2[C:23]([CH3:53])=[CH:24][N:25]([CH:50]([CH3:52])[CH3:51])[C:26]=2[CH:27]=[C:28]([C:30]2[CH:35]=[N:34][C:33]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][C@H:37]3[CH3:49])=[CH:32][CH:31]=2)[CH:29]=1)=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68210133(R)-tert-Butyl 4-(5-(4-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-3-methyl-1H-indol-6-yl)pyridin-2-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 67468650HCID 67468650, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Added trifluoroacetic acid (1 ml, 12.98 mmol) to a solution of (R)-tert-butyl 4-(5-(4-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-3-methyl-1H-indol-6-yl)pyridin-2-yl)-3-methylpiperazine-1-carboxylate (57 mg, 0.091 mmol) in DCM (3 mL) and let stir at RT for 1 hour. Concentrated on rotovap. Partitioned between DCM and sat'd Na2CO3, separated and washed DCM phase with water, brine, dried (MgSO4), filtered and rotovapped off DCM. Obtained 25 mg of the title compound as a tan solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.19 (d, 2H), 1.46-1.59 (m, 6H), 2.21 (s, 3H), 2.27 (s, 3H), 2.44 (s, 3H), 2.83 (dd, J=12.13, 3.54 Hz, 1H), 2.96-3.29 (m, 4H), 3.90 (br. s., 1H), 4.47-4.76 (m, 5H), 6.00 (s, 1H), 6.51 (d, J=8.59 Hz, 1H), 7.05 (s, 1H), 7.45 (s, 1H), 7.68 (dd, J=8.72, 2.40 Hz, 1H), 8.43 (d, J=2.27 Hz, 1H), 10.11-12.70 (m, 1H). LCMS: [M+H]+ 527.5.

Workup

  1. concentrationConcentrated on rotovap
  2. customPartitioned between DCM
  3. customseparated
  4. washwashed DCM phase with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-93d858498e20447fb96fd0a8e6dc9022
Source dataset
uspto-grants-2016_08
Patent number
US09402836B2

Reaction notes

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