Trifluoroacetic acid → HCID 59451416, compound

HRID 1874791Notes

Reaction equation

HRID 1874791 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([O:28][CH2:29][C@@H:30]2[O:35][CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]2)=[CH:23][CH:22]=3)=[O:18])=[C:11]([F:43])[C:10]=1[O:44][C:45]1[CH:50]=[C:49]([C:51]#[N:52])[CH:48]=[C:47]([Cl:53])[CH:46]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([O:28][CH2:29][C@@H:30]2[O:35][CH2:34][CH2:33][NH:32][CH2:31]2)=[CH:23][CH:22]=3)=[O:18])=[C:11]([F:43])[C:10]=1[O:44][C:45]1[CH:50]=[C:49]([C:51]#[N:52])[CH:48]=[C:47]([Cl:53])[CH:46]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59451433HCID 59451433, compound

Product 1

HCID 59451416HCID 59451416, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) and CH2Cl2 (2 mL) were added to 1,1-dimethylethyl (2R)-2-{[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)oxy]methyl}-4-morpholinecarboxylate (0.02 g, 0.03 mmol) and the mixture was stirred for 1 h. The solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were neutralized with saturated NaHCO3 and extracted with EtOAc. The organic extracts were combined dried over Na2SO4, filtered and evaporated to afford the title compound (0.015 g, 88%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.51 (br. s., 1H), 9.00 (t, 1H), 7.74-7.89 (m, 1H), 7.44-7.56 (m, 3H), 7.33-7.44 (m, 1H), 7.26-7.33 (m, 1H), 7.01-7.13 (m, 2H), 6.72-6.92 (m, 1H), 4.49-4.60 (m, 2H), 3.85-4.02 (m, 4 H), 3.59-3.71 (m, 1H), 3.15-3.24 (m, 1H), 2.98-3.08 (m, 1H), 2.77-2.97 (m, 2 H). MS: m/z 569.1 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customPurification
  3. extractionextracted with EtOAc
  4. dry with materialThe organic extracts were combined dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3dfd94af621443ea8d286d5f49da7c76
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…