Trifluoroacetic acid → HCID 67276893, compound

HRID 1698059Notes

Reaction equation

HRID 1698059 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:33]=[CH:32][C:9]2[N:10]=[C:11]([C:13]3[CH:14]=[N:15][C:16]([N:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[CH:17][CH:18]=3)[S:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35].C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[N:19]1([C:16]2[N:15]=[CH:14][C:13]([C:11]3[S:12][C:8]4[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:33]=[CH:32][C:9]=4[N:10]=3)=[CH:18][CH:17]=2)[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57553392HCID 57553392, compound

Product 1

HCID 67276893HCID 67276893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[6-[4-[(1,1-Dimethylethoxy)carbonyl]-1-piperazinyl]-3-pyridinyl]-6-benzothiazolecarboxylic acid ethyl ester (0.42 g, 0.90 mmol) was dissolved in DCM (35 mL) and TFA (2 mL) was added. The reaction was stirred at r.t. for 3 days. Sat. sodium hydrogencarbonate was added to the mixture. The precipitate was collected, followed by washing with DCM and water, before drying in vacuo over P2O5 to give the title compound (0.34 g) as a yellow solid. 1H NMR δ 8.82-8.93 (m, 3H) 8.76 (s, 1H) 8.27 (dd, 1H) 8.07 (d, 2H) 7.11 (d, 1H) 4.37 (q, 2H) 3.84-3.95 (m, 4H) 3.23 (br. s., 4H) 1.36 (t, 3H); MS m/z (M+H) 369.

Workup

  1. customThe precipitate was collected
  2. washby washing with DCM and water
  3. dry with materialbefore drying in vacuo over P2O5

Sources & evidence

ORD record
ord-466fe35c3d174f58b25bcc8eea52a88c
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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