Trifluoroacetic acid → HCID 86658431, compound

HRID 1968895Notes

Reaction equation

HRID 1968895 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:13][N:14]([C:26]([C@H:28]1[CH2:30][C@@H:29]1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[N:32]=1)=[O:27])[C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=1)[C@@H:9]([CH3:12])[CH2:10][CH3:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@@H:8]([C@@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:13][N:14]([C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=1)[C:26]([C@H:28]1[CH2:30][C@@H:29]1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[N:32]=1)=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67436425HCID 67436425, compound

Product 1

HCID 86658431HCID 86658431, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((1S,2S)-1-{[[(1S,2S)-2-(6-Fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-(4-pent-1-ynyl-phenyl)-amino]-methyl}-2-methyl-butyl)-carbamic acid t-butyl ester (0.0657 g, 0.126 mmol), trifluoroacetic acid (1 mL) and dichloromethane (2 mL) were mixed at 0° C., then stirred at room temperature for 1 hr. The excessive solvent was removed in vacuum. The residue was purified by preparatory HPLC to give a white solid (0.0277 g, 34%): 1H NMR (400 MHz, MeOD) δ ppm 7.66 (m, 1H), 7.24 (m, 4H), 7.07 (td, J=7.1, 2.3 Hz, 1H), 6.66 (m, 1H), 4.16 (m, 1H), 3.58 (m, 1H), 3.21 (dt, J=3.3, 1.6 Hz, 1H), 2.47 (br. s., 1H), 2.29 (td, J=7.0, 3.2 Hz, 2H), 1.81 (dd, J=5.3, 3.5 Hz, 1H), 1.62 (m, 1H), 1.53 (m, 3H), 1.29 (m, 2H), 1.10 (m, 1H), 0.95 (td, J=7.3, 2.5 Hz, 3H), 0.86 (dd, J=7.1, 4.8 Hz, 3H), 0.73 (m, 3H); LCMS (ESI) m/e 422.3 [(M+H)+, calcd for C26H33FN3O 422.6].

Workup

  1. customThe excessive solvent was removed in vacuum
  2. customThe residue was purified by preparatory HPLC

Sources & evidence

ORD record
ord-1c5ba10c60284a33be91703d7239586f
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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