Trifluoroacetic acid → HCID 69631096, compound

HRID 625336Notes

Reaction equation

HRID 625336 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=2)[CH2:16][S:17][CH2:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:12])=[C:6]([C:30]2[CH:35]=[C:34]([C:36](=[O:49])[NH:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=3)[CH:33]=[CH:32][N:31]=2)[CH:5]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=2)[CH2:16][S:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:12])=[C:6]([C:30]2[CH:35]=[C:34]([C:36](=[O:49])[NH:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:47])([F:48])[F:46])[CH:40]=3)[CH:33]=[CH:32][N:31]=2)[CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66586777HCID 66586777, compound

Product 1

HCID 69631096HCID 69631096, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 3-(3-(4-(ethylthio)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)propanoate (200 mg, 0.28 mmol, 1.00 equiv) in dichloromethane (5 mL), and trifluoroacetic acid (2 mL). The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The crude product (0.2 g) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained 40.4 mg (21%) of a light yellow solid. 1H-NMR (400 MHz, DMSO-d6, ppm): δ 12.85 (s, 1H), 12.28 (s, 1H), 9.60-9.57 (m, 1H), 9.01-8.99 (m, 1H), 8.55-8.53 (m, 1H), 8.39 (s, 1H), 7.96-7.51 (m, 11H), 4.65-4.64 (d, J=5.2 Hz, 2H), 3.90 (s, 2H), 3.08-3.03 (m, 2H), 2.63-2.59 (t, J=5.1 Hz, 2H), 1.28-1.24 (t, J=5.7 Hz, 3H). MS (ES, m/z): 654 [M+H]+.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe crude product (0.2 g) was purified by reverse phase HPLC
  4. washeluting with a water/CH3CN gradient
  5. additioncontaining 0.05% TFA

Sources & evidence

ORD record
ord-06108b4bb6e64df2a702794370033236
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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