Trifluoroacetic acid → HCID 56966291, compound

HRID 1408046Notes

Reaction equation

HRID 1408046 reaction equation
[F:1][C:2]([F:51])([F:50])[C:3]1[CH:4]=[C:5]([CH:47]=[CH:48][CH:49]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:21]=[C:20]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[NH:27][C:28]([C:30]2[CH:31]=[C:32]([CH:44]=[CH:45][CH:46]=2)[CH2:33][S:34][CH2:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])=[O:29])[CH:11]=1)=[O:9].FC(F)(F)C(O)=O>ClCCl>[N:22]1([C:20]2[CH:19]=[CH:18][C:17]([NH:27][C:28]([C:30]3[CH:31]=[C:32]([CH:44]=[CH:45][CH:46]=3)[CH2:33][S:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:29])=[C:16]([C:12]3[CH:11]=[C:10]([C:8](=[O:9])[NH:7][CH2:6][C:5]4[CH:47]=[CH:48][CH:49]=[C:3]([C:2]([F:51])([F:1])[F:50])[CH:4]=4)[CH:15]=[CH:14][N:13]=3)[CH:21]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66586815HCID 66586815, compound

Product 1

HCID 56966291HCID 56966291, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 50-mL round bottom flask, was placed a solution of tert-butyl 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(pyrrolidin-1-yl)phenyl)carbamoyl)-benzylthio)propano ate (600 mg, 0.84 mmol, 1.00 equiv) in dichloromethane (20 mL), and trifluoroacetic acid (2 mL). The resulting solution was stirred for 2.5 h at 25° C. in an oil bath. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The crude product (120 mg) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 96.2 mg (15%) of a yellow solid. 1H-NMR (300 MHz, DMSO, ppm): δ 11.92 (s, 1H), 9.51 (t, J=11.7 Hz, 1H), 8.95 (d, J=5.4 Hz, 1H), 8.28 (s, 1H), 8.15 (d, J=8.7 Hz, 1H), 7.82 (d, J=5.4 Hz, 2H), 7.73 (t, J=12.3 Hz, 2H), 7.55 (m, 5H), 6.96 (d, J=2.4 Hz, 1H), 6.76 (m, 1H), 4.62 (d, J=5.7 Hz, 2H), 3.87 (s, 2H), 3.33 (s, 4H), 2.62 (m, 2H), 2.50 (m, 2H), 1.99 (s, 4H). MS (ES, m/z): 663 [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 (120 mg) was purified by reverse phase HPLC
  4. washeluting with a water/CH3CN gradient
  5. additioncontaining 0.05% TFA

Sources & evidence

ORD record
ord-bd4ee79929a5469ba084faf5142ad4a9
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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