Trifluoroacetic acid → HCID 23585763, compound

HRID 1268845Notes

Reaction equation

HRID 1268845 reaction equation
[C:1]1([C:6]2[S:14][C:13]3[C:12]([C:15]([NH2:17])=[O:16])=[CH:11][N:10]=[C:9]([NH:18]CC4C=CC(OC)=CC=4)[C:8]=3[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C(O)(C(F)(F)F)=O>>[NH4+:10].[OH-:16].[NH2:18][C:9]1[C:8]2[CH:7]=[C:6]([C:1]3[CH2:5][CH2:4][CH2:3][CH:2]=3)[S:14][C:13]=2[C:12]([C:15]([NH2:17])=[O:16])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58840748HCID 58840748, compound

Product 2

HCID 14923Ammonium HydroxideHCID 23585763HCID 23585763, compoundYield 15.4%

Conditions

Temperature
50 °C

Procedure

To 2-cyclopent-1-enyl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carboxylic acid amide 33 (21 mg, 0.055 mmol.) was added TFA (2 mL) and the solution was heated to 50° C. for 1 h. Solvents were removed in vacuo. Silica gel column chromotagraphy (eluent: 1 NH4OH, 7% MeOH in CH2Cl2) provided 1.1 mg of 34. 1H NMR (400 MHz, d6-DMSO) δ 8.46 (s, 1H), 7.89 (bs, 1H), 7.51 (s, 1H), 7.24 (bs, 1H), 7.12 (bs, 2H), 6.15 (m,1H), 2.72 (m, 2H), 2.53 (m, 2H), 2.01 (p, J=7 Hz, 2H).

Workup

  1. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-db109d14ab4b478fbc0386d58059a908
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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