HCID 59551951, compound → HCID 11495366, compound

HRID 1170494Notes

Reaction equation

HRID 1170494 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11](C(OC(C)(C)C)=O)[CH2:12][CH2:13][CH2:14][N:15]([CH2:26][C:27]([OH:29])=[O:28])[C:16]3[S:20][N:19]=[C:18]([N:21]4[CH:25]=[CH:24][N:23]=[CH:22]4)[N:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:26][C:27]([OH:29])=[O:28])[C:16]3[S:20][N:19]=[C:18]([N:21]4[CH:25]=[CH:24][N:23]=[CH:22]4)[N:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 1

HCID 59551951HCID 59551951, compound

Product 1

HCID 11495366HCID 11495366, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

[[3-(Benzo[1,3]dioxol-5-ylmethyl-tert-butoxycarbonyl-amino)-propyl]-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-amino]-acetic acid (70 mg, 140 μmol) was dissolved in TFA/DCM (1:1, 2 mL) and stirred at room temperature for 30 min. SiO2 (3 g) was added and the solvent was evaporated to afford a white slurry. Purification was achieved using column chromatography (CH2Cl2 to 4:1 CH2Cl2/MeOH) to afford 58 mg (99%) of [{3-[(benzo[1,3]dioxol-5-ylmethyl)-amino]-propyl}-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-amino]-acetic acid as a white solid. [M+H]+ 416.92; 1H NMR (400 MHz, d6-DMSO) δ 9.05 (s, 1H), 8.79 (br s, 1H), 8.00 (s, 1H), 7.49 (s, 1H), 7.06 (s, 1H), 6.97 (m, 2H), 6.06 (s, 2H), 4.39 (br s, 2H), 4.26 (s, 2H), 3.66 (m, 2H), 3.00 (m, 2H), 2.01 (m, 2H).

Workup

  1. customthe solvent was evaporated
  2. customto afford a white slurry
  3. customPurification

Sources & evidence

ORD record
ord-f337ddd252104d0086d76662c8cf87f1
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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