Triethylamine → HCID 58182720, compound

HRID 1361481Notes

Reaction equation

HRID 1361481 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][N:12]=[C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:10]=1.C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29]>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][N:12]=[C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29])[CH2:16][CH2:15]2)[N:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 58182721HCID 58182721, compound

Product 1

HCID 58182720HCID 58182720, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(5-(2-methoxyphenyl)-1,2,4-thiadiazol-3-yl)piperazine (80 mg, 0.29 mmol) and triethylamine (61 μL, 0.43 mmol) in CH2Cl2 (0.5 mL) at 0° C. was added isobutyl chloroformate (59 mg, 0.43 mmol) in CH2Cl2 (0.5 mL). The reaction mixture was stirred at 0° C. for 1 h, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield isobutyl 4-(5-(2-methoxyphenyl)-1,2,4-thiadiazol-3-yl)piperazine-1-carboxylate. LC/MS: m/z 377.5 (M+H)+ at 3.81 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8d670c9aee742d3b6f45ca041129fb3
Source dataset
uspto-grants-2011_02
Patent number
US07880008B2

Reaction notes

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