Trifluoroacetic acid → HCID 178457133, compound

HRID 1443395Notes

Reaction equation

HRID 1443395 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:37][CH:38]([CH3:40])[CH3:39])[C:14]([N:16]2[CH:25]([C:26]3[NH:27][CH:28]=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:30]=3)[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17]2)=[O:15])=[CH:8][CH:7]=1)(C)(C)C.FC(F)(F)C(O)=O>>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:37][CH:38]([CH3:40])[CH3:39])[C:14]([N:16]2[CH:25]([C:26]3[NH:27][CH:28]=[C:29]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:30]=3)[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17]2)=[O:15])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178457134HCID 178457134, compound

Product 1

HCID 178457133HCID 178457133, compound

Procedure

3-(4-tert-Butoxy-phenyl)-2-isopropylamino-1-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-propan-1-one (0.086 g, 0.16 mmol) was added to ice cooled trifluoroacetic acid (3 mL). After 1.5 hour the reaction was concentrated under reduced pressure to give a clear oil. This material was purified via a Gilson preparative HPLC resulting in the isolation of desired product 3-(4-hydroxy-phenyl)-2-isopropylamino-1-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-propan-1-one as a white solid after lyophilization, which proved 100% pure by HPLC at 254 and 214 nm, (LC/MS; Measured MW (MH+): 481).

Workup

  1. concentrationAfter 1.5 hour the reaction was concentrated under reduced pressure
  2. customto give a clear oil
  3. customThis material was purified via a Gilson preparative HPLC

Sources & evidence

ORD record
ord-50c3c96a45ab49799931bfaca198ae16
Source dataset
uspto-grants-2010_02
Patent number
US07659402B2

Reaction notes

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