Trifluoroacetic acid → Trifluoroacetic acid

HRID 1783768Notes

Reaction equation

HRID 1783768 reaction equation
C(OC(=O)[NH:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[C:20]2[C:15](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=2)[C:14]2=[N:25][NH:26][C:27](=[O:28])[N:13]2[CH:12]=1)(C)(C)C.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]>ClCCl>[NH2:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[C:20]2[C:15](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=2)[C:14]2=[N:25][NH:26][C:27](=[O:28])[N:13]2[CH:12]=1.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57590935HCID 57590935, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 17747016HCID 17747016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl[(2E)-3-(3-oxo-2,3-dihydrobenzo[g][1,2,4]triazolo[3,4-a]isoquinolin-6-yl)prop-2-en-1-yl]carbamate (7-7) (3.0 mg, 0.0077 mmol) in a ¼ mixture of dichloromethane and TFA (1.0 ml) was stirred at room temperature for 15 min and concentrated to dryness to give the deprotected material 7-8 as a TFA salt. LRMS m/z: found 291.1, calcd. (M+H) 291.1. 1H NMR (500 MHz, CD3OD) δ: 3.88 (d, J=6.6 Hz, 2H), 6.35 (dt, J=6.6, 15.6 Hz, 1H), 7.31 (d, J=15.7 Hz, 1H), 7.63 (s, 1H), 7.65-7.68 (m, 2H), 8.05-8.11 (m, 2H), 8.38 (s, 1H), 8.84 (s, 1H).

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4526d712568842058b2509899892207c
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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