HCID 59551899, compound → HCID 11646432, compound

HRID 1170468Notes

Reaction equation

HRID 1170468 reaction equation
C(OC(=O)[N:7]([CH2:23][C:24]1[CH:32]=[CH:31][C:27]2[O:28][CH2:29][O:30][C:26]=2[CH:25]=1)[CH2:8][CH2:9][CH2:10][N:11]([C:13]1[S:17][N:16]=[C:15]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[N:14]=1)[CH3:12])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([CH2:23][NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:13]3[S:17][N:16]=[C:15]([N:18]4[CH:22]=[CH:21][N:20]=[CH:19]4)[N:14]=3)[CH3:12])=[CH:25][C:26]=2[O:30][CH2:29]1

Participants

3

Reactant 1

HCID 59551899HCID 59551899, compound

Product 1

HCID 11646432HCID 11646432, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of benzo[1,3]dioxol-5-ylmethyl-{3-[(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester (10.6 g, 22.4 mmol) in TFA/DCM (50%, 70 mL) was stirred at room temperature for 30 min. The solvent was evaporated and a saturated solution of potassium carbonate (50 mL) was added to make it basic (pH 9). The solution was extracted with ethyl acetate (2×200 mL), washed with brine and dried over Na2SO4. Evaporation of the solvent gave 8.30 g (99%) of N′-benzo[1,3]dioxol-5-ylmethyl-N-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-N-methyl-propane-1,3-diamine as a colorless oil. [M+H]+ 373.26; 1H-NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), 7.63 (s, 1H), 7.07 (s, 1H), 6.79 (s, 1H), 6.72 (s, 2H), 5.92 (s, 2H), 3.67 (s, 3H), 3.60 (br s, 1H), 3.10 (br s, 2H), 2.66 (t, 2H), 2.0 (br s, 2H), 1.87 (q, 2H); 13C-NMR (100 MHz, CD3OD) δ 184.3, 156.7, 147.7, 146.6, 136.4, 133.8, 129.9, 121.2, 117.1, 108.6, 108.1, 100.9, 53.7, 45.7, 27.1.

Workup

  1. customThe solvent was evaporated
  2. additiona saturated solution of potassium carbonate (50 mL) was added
  3. extractionThe solution was extracted with ethyl acetate (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7fc2df3eb14a44128fcc5aba8aafee55
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

Loading…