Trifluoroacetic acid → HCID 86644910, compound

HRID 1875024Notes

Reaction equation

HRID 1875024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([NH:21][C:22]([C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][N:25]2C(OC(C)(C)C)=O)=[O:23])=[CH:16][CH:15]=3)=[O:11])=[C:4]([F:37])[C:3]=1[O:38][C:39]1[CH:44]=[C:43]([C:45]#[N:46])[CH:42]=[C:41]([Cl:47])[CH:40]=1.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>ClCCl>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([NH:21][C:22]([C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]2)=[O:23])=[CH:16][CH:15]=3)=[O:11])=[C:4]([F:37])[C:3]=1[O:38][C:39]1[CH:44]=[C:43]([C:45]#[N:46])[CH:42]=[C:41]([Cl:47])[CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86644909HCID 86644909, compound

Product 1

HCID 86644910HCID 86644910, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S)-2-{[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)amino]carbonyl}-1-piperidinecarboxylate (0.025 g, 0.036 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (0.5 mL, 6.49 mmol). The mixture was stirred at room temperature for 1 hr. The solvent was evaporated and the residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA) to give the title compound (0.012 g, 47%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.63 (br. s., 1H), 10.29 (s, 1H), 8.94-9.03 (m, 1H), 8.82-8.94 (m, 1H), 8.62-8.79 (m, 1H), 7.90 (s, 1H), 7.78 (s, 1H), 7.41-7.52 (m, 2H), 7.30-7.41 (m, 1H), 7.24 (d, 1H), 7.11 (s, 1H), 4.53 (d, 2H), 3.74-3.88 (m, 1H), 3.16-3.31 (m, 1H), 2.85-3.02 (m, 1H), 2.10-2.24 (m, 1H), 1.74-1.88 (m, 1H), 1.41-1.75 (m, 4H). ES MS: m/z 580 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA)

Sources & evidence

ORD record
ord-5fdbae9452bb48b5901c2e44459b00e2
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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