Ammonia → HCID 11546144, compound

HRID 1170493Notes

Reaction equation

HRID 1170493 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH2:17][CH2:18][CH2:19][N:20]([CH2:28][C:29]1[CH:37]=[CH:36][C:32]2[O:33][CH2:34][O:35][C:31]=2[CH:30]=1)C(OC(C)(C)C)=O)[C:7]1[S:11][N:10]=[C:9]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[N:8]=1)C.[NH3:39]>CO.CCOC(C)=O>[O:33]1[C:32]2[CH:36]=[CH:37][C:29]([CH2:28][NH:20][CH2:19][CH2:18][CH2:17][N:6]([C:7]3[S:11][N:10]=[C:9]([N:12]4[CH:16]=[CH:15][N:14]=[CH:13]4)[N:8]=3)[CH2:5][C:4]([NH2:39])=[O:3])=[CH:30][C:31]=2[O:35][CH2:34]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 59551926HCID 59551926, compound

Product 1

HCID 11546144HCID 11546144, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [[3-(benzo[1,3]dioxol-5-ylmethyl-tert-butoxycarbonyl-amino)-propyl]-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-amino]-acetic acid ethyl ester from Step 1 (115 mg, 211 μmol) and a 2.0 M solution NH3 in MeOH (10 mL) was stirred at r.t. for 24 h. The reaction mixture was concentrated to a yellow oil. The crude residue was dissolved in TFA/DCM (1:1, 3 mL) and stirred at room temperature for 30 min. The solvent was evaporated to afford an orange oil. The crude product was diluted with EtOAc (50 mL), washed with 1M NaOH (50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated to an oil. Purification was achieved using column chromatography (CH2Cl2 to 4:1 CH2Cl2/MeOH) to afford 53 mg (60%) of 2-[{3-[(benzo[1,3]dioxol-5-ylmethyl)-amino]-propyl}-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-amino]-acetamide as a white solid. [M+H]+ 415.97; 1H NMR (400 MHz, d6-DMSO) δ 8.29 (s, 1H), 7.72 (s, 1H), 7.63 (br s, 1H), 7.28 (br s, 1H), 7.09 (s, 1H), 6.92 (s, 1H), 6.82 (m, 2H), 5.98 (s, 2H), 4.20 (br s, 1H), 3.60 (s, 2H), 3.33 (s, 2H), 2.54 (m, 4H), 1.80 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated to a yellow oil
  2. dissolutionThe crude residue was dissolved in TFA/DCM (1:1, 3 mL)
  3. customThe solvent was evaporated
  4. customto afford an orange oil
  5. washwashed with 1M NaOH (50 mL), brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customPurification

Sources & evidence

ORD record
ord-6e00ef43223e4b8bb95cba553aadd5a6
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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