HCID 68452001, compound → HCID 11271024, compound

HRID 2353369Notes

Reaction equation

HRID 2353369 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:35]=[CH:34][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:20]([C:30]([F:33])([F:32])[F:31])[CH:19]=3)[S:17][C:13]=2[CH:12]=1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:32][C:30]([F:31])([F:33])[C:20]1[CH:19]=[C:18]([C:16]2[S:17][C:13]3[CH:12]=[C:11]([CH2:10][NH:9][CH2:8][CH2:7][C:6]([OH:36])=[O:5])[CH:35]=[CH:34][C:14]=3[N:15]=2)[CH:23]=[CH:22][C:21]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 1

HCID 68452001HCID 68452001, compound

Product 1

HCID 11271024HCID 11271024, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3-{[2-(2-Trifluoromethyl-biphenyl-4-yl)-benzothiazol-6-ylmethyl]-amino}-propionic acid tert-butyl ester (31 mg, 0.0605 mmol) is dissolved in TFA/CH2Cl2 (1/1) (1 mL). The solution is stirred at room temperature for an hour. The mixture is concentrated and purified by reversed phase preparative LC/MS to give 10 mg of 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-benzothiazol-6-ylmethyl]-amino}-propionic acid: 1H NMR (CD3OD, 400 MHz) δ 8.54 (s, 1H), 8.35 (d, 1H), 8.22 (s, 1H), 8.18 (d, 2H), 7.68 (d, 1H), 7.45 (m, 3H), 7.37 (m, 2H), 4.44 (s, 2H), 3.36 (m, 2H), 2.80 (m, 2H); MS (ES+) 457.0 (M+H+).

Workup

  1. concentrationThe mixture is concentrated
  2. custompurified by reversed phase preparative LC/MS

Sources & evidence

ORD record
ord-13e77fb8bbcb4d26b834cdffc87b45c5
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

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