Trifluoroacetic acid → Trifluoroacetic acid

HRID 1096672Notes

Reaction equation

HRID 1096672 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[CH:15]1[CH2:20][CH:19]([CH3:21])[CH2:18][N:17]([C:22](=[O:44])[CH2:23][C@H:24]([NH:36]C(=O)OC(C)(C)C)[CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH2:16]1.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>>[NH2:36][C@H:24]([CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)[CH2:23][C:22]([N:17]1[CH2:18][CH:19]([CH3:21])[CH2:20][CH:15]([C:7]2[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)[CH2:16]1)=[O:44].[C:47]([OH:49])([C:46]([F:51])([F:50])[F:45])=[O:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66791927HCID 66791927, compound

Product 2

HCID 6422Trifluoroacetic acidYield 9%HCID 66785403HCID 66785403, compound

Procedure

The residue 136H 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 (25-35% CH3CN in H2O) to give (3R)-3-amino-1-(3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)-5-methylpiperidin-1-yl)-4-(naphthalen-2-yl)butan-1-one (246) as a TFA salt (13 mg, 9%). ESI-MS:m/z 499.5 (M+H)+.

Workup

  1. customSolvent was removed under vacuum
  2. custompurified by preparatory LC/MS (25-35% CH3CN in H2O)

Sources & evidence

ORD record
ord-d4257fdcb86141d3ae7cbf6b7a334ca6
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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