Trifluoroacetic acid → Trifluoroacetic acid

HRID 1096669Notes

Reaction equation

HRID 1096669 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:39])[CH2:18][C@H:19]([NH:31]C(=O)OC(C)(C)C)[CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)[CH2:12]2)[C:9]2[CH:40]=[CH:41][CH:42]=[CH:43][C:8]=2[N:7]=1.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>>[NH2:31][C@H:19]([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[CH2:18][C:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@@H:11]([N:10]2[C:9]3[CH:40]=[CH:41][CH:42]=[CH:43][C:8]=3[N:7]=[C:6]2[CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:12]1)=[O:39].[C:46]([OH:48])([C:45]([F:50])([F:49])[F:44])=[O:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86761538HCID 86761538, compound

Product 2

HCID 6422Trifluoroacetic acidYield 24%HCID 66785732HCID 66785732, compound

Procedure

134F was dissolved in 25% trifluoroacetic acid and stirred at room temperature for 3 hr. Solvent was removed under vacuum and purified by preparatory LC/MS (20-25% CH3CN in H2O) to give (R)-3-amino-1((R)-3-(2-(3-methoxypropyl)-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)-4-(naphthalen-2-yl)butan-1-one (243) as a TFA salt (97 mg, 24%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62 (m, 1H) 1.86 (br. s., 1H) 1.97-2.15 (m, 3H) 2.53-2.91 (m, 3H) 2.94-3.26 (m, 7H) 3.40 (m, 3H) 3.75-4.10 (m, 3H) 4.42-4.71 (m, 2H) 7.50 (m, 5H) 7.72-7.96 (m, 5H) 8.21 (m, 1H). ESI-MS:m/z 485.5 (M+H)+.

Workup

  1. customSolvent was removed under vacuum
  2. custompurified by preparatory LC/MS (20-25% CH3CN in H2O)

Sources & evidence

ORD record
ord-9efa10b8a1c14ee48ffc75847dbe1425
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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